publications i. jabin - ulb.ac.be i. jabin ... enantioselective synthesis of c 2-symmetric cis- ......

12
1 PUBLICATIONS I. JABIN 1- "Michael reaction of functionalized chiral cyclanone imines. Enantioselective synthesis of C 2 - symmetric cis-(1R,6R)-1,6-dimethylbicyclo[4.4.0]decane-3,8-dione" Pfau, M.; Jabin, I.; Revial, G. J. Chem. Soc. Perkin Trans. 1 1993, 17, 1935-1936. 2- "Diastereoselectivity and enantioselectivity in the addition of chiral imines of 2-methylcyclohexanone to crotonic and methacrylic acid esters" Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymm. 1995, 6, 1795-1812. 3- "Enantioselective syntheses of (2S,4aS,8aR)-1,1,4a-trimethyldecahydronaphtha- len-2-ol [(–)-TMD], (4aS,8aR)-5,5,8a-trimethyloctahydronaphthalen-2(1H)-one, and (–)-Polywood , through Michael- type reaction of chiral imines" Jabin, I.; Revial, G.; Melloul, K.; Pfau, M. Tetrahedron: Asymm. 1997, 8, 1101-1109. 4- "Reaction of cyclohexanones imines with substituted nitroolefins. New synthesis of tetrahydroindole derivatives" Lim, S.; Jabin, I.; Revial, G. Tetrahedron Lett. 1999, 40, 4177-4180. 5- "Tautomerism of ,-ethylenic imines and their reactivity toward electrophilic olefins" Jabin, I.; Revial, G.; Pfau, M.; Decroix, B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904. 6- "Synthetic approaches to 3-substituted-5'-(N-pyridiniummethyl)-4',5'-dihydropsoralen" Jabin, I.; Heindel, N.D.; Rapp, R.D.; Laskin, J.D. J. Het. Chem. 2000, 37, 31-39. 7- "Enantioselective synthesis of (+)--vetivone through the Michael reaction of chiral imines" Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymm. 2000, 11, 4975-4983. 8- "Reaction of Cyclohexanone Benzylimines with Ethylidenemalonate Diesters. Diphenyl 2- ethylidenemalonate: a Highly Electrophilic Synthetic Equivalent of Crotonic Esters" Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261. 9- "Enantioselective Imine Michael Reaction for the Preparation of the (8'R,8a'S)-8,8a'-Dimethyl- 1',3',4',7',8',8a'-hexahydrospiro[1,3-dioxolane-2,2'(6'H)naphthalen]-6'-one Building Block. A formal synthesis of (+)-Valencenol" Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron: Asymm. 2001, 12, 1683-1688. 10- "Synthetic approaches to 4,8-dimethyl-5'-(N-pyridiniummethyl)-4',5'-dihydropsoralens and 4,8- dimethyl-5'-(N-aminomethyl)-4',5'-dihydropsoralensWhittemore, M.S.; Heindel, N.D.; Jabin, I.; Guillon, C.; McNeel, T.E.; Rapp, R.D.; Heck, D.E.; Laskin, J.D. J. Het. Chem. 2001 38, 909-916.

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Page 1: PUBLICATIONS I. JABIN - ulb.ac.be I. JABIN ... Enantioselective synthesis of C 2-symmetric cis- ... 7-"Enantioselective synthesis of (+)- -vetivone through the Michael reaction of

1

PUBLICATIONS I. JABIN

1- "Michael reaction of functionalized chiral cyclanone imines. Enantioselective synthesis of C2-

symmetric cis-(1R,6R)-1,6-dimethylbicyclo[4.4.0]decane-3,8-dione"

Pfau, M.; Jabin, I.; Revial, G. J. Chem. Soc. Perkin Trans. 1 1993, 17, 1935-1936.

2- "Diastereoselectivity and enantioselectivity in the addition of chiral imines of 2-methylcyclohexanone

to crotonic and methacrylic acid esters"

Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymm. 1995, 6, 1795-1812.

3- "Enantioselective syntheses of (2S,4aS,8aR)-1,1,4a-trimethyldecahydronaphtha- len-2-ol [(–)-TMD],

(4aS,8aR)-5,5,8a-trimethyloctahydronaphthalen-2(1H)-one, and (–)-Polywood, through Michael-

type reaction of chiral imines"

Jabin, I.; Revial, G.; Melloul, K.; Pfau, M. Tetrahedron: Asymm. 1997, 8, 1101-1109.

4- "Reaction of cyclohexanones imines with substituted nitroolefins. New synthesis of tetrahydroindole

derivatives"

Lim, S.; Jabin, I.; Revial, G. Tetrahedron Lett. 1999, 40, 4177-4180.

5- "Tautomerism of ,-ethylenic imines and their reactivity toward electrophilic olefins"

Jabin, I.; Revial, G.; Pfau, M.; Decroix, B.; Netchitaïlo, P. Org. Lett. 1999, 1, 1901-1904.

6- "Synthetic approaches to 3-substituted-5'-(N-pyridiniummethyl)-4',5'-dihydropsoralen"

Jabin, I.; Heindel, N.D.; Rapp, R.D.; Laskin, J.D. J. Het. Chem. 2000, 37, 31-39.

7- "Enantioselective synthesis of (+)--vetivone through the Michael reaction of chiral imines"

Revial, G.; Jabin, I.; Pfau, M. Tetrahedron: Asymm. 2000, 11, 4975-4983.

8- "Reaction of Cyclohexanone Benzylimines with Ethylidenemalonate Diesters. Diphenyl 2-

ethylidenemalonate: a Highly Electrophilic Synthetic Equivalent of Crotonic Esters"

Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P. J. Org. Chem. 2001, 66, 256-261.

9- "Enantioselective Imine Michael Reaction for the Preparation of the (8'R,8a'S)-8,8a'-Dimethyl-

1',3',4',7',8',8a'-hexahydrospiro[1,3-dioxolane-2,2'(6'H)naphthalen]-6'-one Building Block. A formal

synthesis of (+)-Valencenol"

Revial, G.; Jabin, I.; Redolfi, M.; Pfau, M. Tetrahedron: Asymm. 2001, 12, 1683-1688.

10- "Synthetic approaches to 4,8-dimethyl-5'-(N-pyridiniummethyl)-4',5'-dihydropsoralens and 4,8-

dimethyl-5'-(N-aminomethyl)-4',5'-dihydropsoralens”

Whittemore, M.S.; Heindel, N.D.; Jabin, I.; Guillon, C.; McNeel, T.E.; Rapp, R.D.; Heck, D.E.; Laskin,

J.D. J. Het. Chem. 2001 38, 909-916.

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11- "A straightforward approach to the galanthan ring system using the imine Michael reaction

followed by a radical cyclization"

Jabin, I.; Netchitaïlo, P. Tetrahedron Lett. 2001, 42, 7823-7827.

12- "Cell-impermeant pyridinium derivatives of psoralens as inhibitors of keratinocyte growth"

Mariano, T.M.; Vetrano, A.M.; Gentile, S.L.; Heck, D.E.; Whittemore, M.S.; Guillon, C.D.; Jabin, I.;

Rapp, R.D.; Heindel, N.D.; Laskin, J.D. Biochemical Pharm. 2002, 63, 31–39.

13- "Use of -aminoesters as chiral auxiliaries in the enantioselective Michael alkylation of chiral

imines"

Jabin, I.; Revial, G.; Pfau, M.; Netchitaïlo, P. Tetrahedron: Asymm. 2002, 13, 563-567.

14- "Aromatization of 1,6,7,7a-tetrahydro-2H-indol-2-ones by a novel process. Preparation of key-

intermediate methyl 1-benzyl-5-methoxy-1H-indole-3-acetate and the syntheses of serotonin,

melatonin, and bufotenin"

Revial, G.; Jabin, I.; Lim, S.; Pfau, M. J. Org. Chem. 2002, 67, 2252-2256.

15- "Reaction of vinyl triflates of -keto esters with primary amines: efficient synthesis of aziridine

carboxylates"

Tranchant, M. J.; Dalla, V.; Jabin, I.; Decroix, B. Tetrahedron 2002, 58, 8425-8432.

16- "Stereoselective synthesis of 5,6-disubstituted-3,4-dihydro-1H-pyridin-2-ones, a new class of non-

biaryl atropisomeric compounds. Part 1"

Jabin, I.; Monnier-Benoit, N.; Le Gac, S.; Netchitaïlo, P. Tetrahedron Lett. 2003, 44, 611-614.

17- "First C3v-symmetrical calix[6](aza)crown"

Jabin, I.; Reinaud, O. J. Org. Chem. 2003, 68, 3416-3419.

18- "Michael reaction of unsubstituted aromatic chiral imines with substituted unsaturated acid esters"

Monnier-Benoit, N.; Jabin, I.; Tomas, A.; Selkti, M.; Revial, G. Tetrahedron: Asymm. 2003, 14, 2747-

2753.

19- "Stereoselective synthesis of new classes of atropisomeric compounds through the tandem imine

Michael reaction-azacyclization process. Part 2" .

Le Gac, S.; Monnier-Benoit, N.; Doumampouom Metoul, L.; Petit, S.; Jabin, I. Tetrahedron: Asymm.

2004, 15, 139-145.

20- Article faisant la couverture du numéro du 23 juillet 2004 du J. Org. Chem.:

"A novel C3v-symmetrical calix[6](aza)cryptand with a remarkably high and selective affinity for small

ammoniums"

Darbost, U.; Giorgi, M.; Reinaud, O.; Jabin, I. J. Org. Chem. 2004, 69, 4879-4884.

21- "A novel receptor based on a C3v-symmetrical PN3-calix[6]cryptand"

Zeng, X.; Hucher, N.; Reinaud, O.; Jabin, I. J. Org. Chem. 2004, 69, 6886-6889.

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22- "X-ray and solution structure of the first Zn funnel complex based on a calix[6]aza-cryptand"

Darbost, U.; Zeng, X.; Rager, M.-N.; Giorgi, M.; Jabin, I.; Reinaud, O. Eur. J. Inorg. Chem. 2004, 4371-

4374.

23- "Synthesis and conformational study of the first triply-bridged calix[6]azatubes"

Le Gac, S.; Zeng, X.; Reinaud, O.; Jabin, I. J. Org. Chem. 2005, 70, 1204-1210.

24- "A calix[6]arene receptor rigidified by a self-assembled tri-ammonium cap: X-ray and NMR

characterization of the binding of polar neutral guests "

Darbost, U.; Giorgi, M.; Hucher, N.; Jabin, I.; Reinaud, O. Supramol. Chem. 2005, 17, 243-250.

25- "Calix[6]tren and Copper(II): A new generation of funnel complexes on the way to redox calix-zymes"

Izzet,G.; Douziech, B.; Prangé, T.; Tomas, A.; Jabin, I.; Le Mest, Y.; Reinaud, O. Proc. Nat. Acad. Sci.

2005, 102, 6831-6836.

26- "Polarizing a hydrophobic cavity for the efficient binding of organic guests: the case of calix[6]tren, a

highly efficient and versatile receptor for neutral or cationic species"

Darbost, U.; Rager, M-.N.; Petit, S.; Jabin, I.; Reinaud, O. J. Am. Chem. Soc. 2005, 127, 8517-8525.

27- "Optically pure calix[6]tris-ammoniums: syntheses and host-guest properties toward neutral guests"

Darbost, U.; Zeng, X.; Giorgi, M.; Jabin, I. J. Org. Chem. 2005, 70, 10552-10560.

28- "First enantiopure calix[6]aza-cryptand: synthesis and chiral recognition properties toward neutral

molecules"

Garrier, E.; Le Gac, S.; Jabin, I. Tetrahedron: Asymm. 2005, 16, 3767-3771.

29- "Allosterically coupled double induced fit for a 1+1+1+1 self-assembly of a calix[6]tris-amine, a

calix[6]tris-acid and their respective guest "

Le Gac, S.; Marrot, J.; Reinaud, O.; Jabin, I. Angew. Chem., Int. Ed. Engl. 2006, 45, 3123-3126.

30- "Efficient synthesis of calix[6]tmpa: a new calix[6]aza-cryptand with unique conformational and

host-guest properties"

Zeng, X.; Coquière, D.; Alenda, A.; Garrier, E.; Prangé, T.; Li, Y.; Reinaud, O.; Jabin, I. Chem. Eur. J.

2006, 12, 6393-6402.

31- "Access to Chiral N-Substituted 1,4-Dihydropyridines Through the One-Pot Domino Michael-

Azacyclization Process"

Monnier-Benoit, N.; Jabin, I.; Netchitaïlo, P. Lett. Org. Chem. 2006, 3, 549-553.

32- "Efficient Synthesis and Host-guest Properties of a New Class of Calix[6]aza-cryptands"

Le Gac, S.; Zeng, X.; Girardot, C.; Jabin, I. J. Org. Chem. 2006, 71, 9233-9236.

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33- "First insights into the electronic properties of a Cu(II) center embedded in the PN3 cap of a

calix[6]arene-based ligand"

Izzet, G.; Zeng, X.; Over, D.; Douziech, B.; Zeitouny, J.; Giorgi, M.; Jabin, I.; Le Mest, Y.; Reinaud, O.

Inorg. Chem. 2007, 46, 375-377.

34- "Allosteric Tuning of the Intra-Cavity Binding Properties of a Calix[6]arene through External Binding

to a ZnII Center Coordinated to Amino Side Chains"

Darbost, U.; Sénèque, O.; Li, Y.; Bertho, G.; Marrot, J.; Rager, M.-N.; Reinaud, O.; Jabin, I. Chem. Eur.

J. 2007, 13, 2078-2088.

35- "Synthesis of 2,4-dimethyl-cyclohex-3-ene carboxaldehyde derivatives with potential olfactory

properties"

Monnier-Benoit P., Jabin I., Jaubert, J.-N.; Netchitaïlo P.; Goyau B. C. R. Chimie 2007, 10, 259-267.

36- Article faisant la couverture de Supramol. Chem.:

"Calix[6]arene Tris-carboxylic Acid Derivatives: X-ray and NMR Characterization of their Remarkable

Host-guest Properties Toward Ammonium Ions"

Le Gac, S.; Giorgi, M.; Jabin, I. Supramol. Chem. 2007, 19, 185-197.

37- Article faisant la couverture de Tetrahedron:

"Self-assembly via ionic interactions of calix[6]arene based receptors displaying remarkable host-

guest properties toward neutral guests"

Le Gac, S.; Luhmer, M.; Reinaud, O.; Jabin, I. Tetrahedron 2007, 63, 10721-10730.

38- "Syntheses and study of calix[6]cryptamides: a novel class of heteroditopic receptors displaying

versatile host-guest properties toward neutral species or organic associated ion-pair salts"

Le Gac, S.; Jabin, I. Chem. Eur. J. 2008, 14, 548-557.

39- "Highly selective synthesis of a 1,3,5-tris-protected calix[6]arene type molecular platform through

coordination and host-guest chemistry"

Le Gac, S.; Marrot, J.; Jabin, I. Chem. Eur. J. 2008, 14, 3316-3322.

40- "Synthesis and host-guest properties of a calix[6]arene based receptor closed by an internal ion-

paired cap"

Richard, J.A.; Pamart, M.; Hucher, N.; Jabin, I. Tetrahedron Lett. 2008, 49, 3848-3852.

41- "Calix[6]tris-(thio)ureas: heteroditopic receptors for the cooperative binding of organic ion-pairs"

Hamon, M.; Ménand, M.; Le Gac, S.; Luhmer, M.; Dalla, V.; Jabin, I. J. Org. Chem. 2008, 73, 7067-

7071.

42- "Dioxygen Activation at a Mononuclear Cu(I) Center Embedded in the Calix[6]arene-Tren Core"

Izzet, G.; Zeitouny, J.; Akdas-Killig, H.; Frapart, Y.; Ménage, S.; Douziech, B.; Jabin, I.; Le Mest, Y.;

Reinaud, O. J. Am. Chem. Soc. 2008, 130, 9514-9523.

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43- "C3v-Symmetrical Calix[6]arenes"

Le Gac, S.; Marrot, J.; Jabin, I. Synfacts 2008, 6, 583.

44- " Second generation of calix[6]aza-cryptands: synthesis of heteroditopic receptors for organic ion

pairs"

Le Gac, S.; Ménand, M.; Jabin, I. Org. Lett. 2008, 10, 5195-5198.

45- "Synthesis of the First Calix[6]crypturea via a Versatile Tris-azide Precursor"

Ménand, M.; Jabin, I. Org. Lett. 2009, 11, 673-676.

46- Article faisant la couverture d'Org. Biomol. Chem.:

"Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules"

Coquière, D.; Le Gac, S.; Darbost, U.; Sénèque, O.; Jabin, I.; Reinaud, O. Org. Biomol. Chem., 2009,

7, 2485–2500.

47- "Induced fit encapsulation by a 1,3,5-alternate calix[6]arene"

Ménand, M.; Leroy, A.; Marrot, J.; Luhmer M.; Jabin, I. Angew. Chem., Int. Ed. Engl. 2009, 48,

5509-5512.

48- "Dramatic Effect of a Protein-like Cavity on Dissociative vs. Associative Copper Redox Chemistry"

Le Poul, N.; Douziech, B.; Zeitouny, J.; Thiabaud, G.; Colas, H.; Conan, F.; Cosquer, N.; Jabin, I.;

Lagrost, C.; Hapiot, P.; Reinaud, O.; Le Mest Y. J. Am. Chem. Soc. 2009, 131, 17800–17807.

49- "Acid-base Controllable Recognition Properties of a Highly Versatile Calix[6]crypturea"

Ménand, M.; Jabin, I. Chem. Eur. J. 2010, 16, 2159-2169.

50- "Calix[6]arene Based Cascade Complexes of Organic Ion-Triplets Stable in a Protic Solvent"

Moerkerke, S; Ménand, M.; Jabin, I. Chem. Eur. J. 2010, 16, 11712-11719.

51- "An Allosteric Heteroditopic Receptor for Neutral Guests and Contact Ion Pairs with a Remarkable

Selectivity for Ammonium Fluoride Salts"

Lascaux, A.; Le Gac, S.; Wouters, J.; Luhmer, M.; Jabin, I. Org. Biomol. Chem. 2010, 8, 4607-4616.

52- "Auto-catalyzed "electroclick" immobilization of a copper complex onto self-assembled

monolayers on a gold electrode"

Gomila, A.; Le Poul, N.; Cosquer, N.; Kerbaol, J.-M.; Noël, J.-M.; Reddy, M. T.; Jabin, I.; Reinaud, O.;

Conan, F.; Le Mest, Y. Dalton Trans. 2010, 39, 11516-11518.

53- Article sélectionné comme Hot Paper (Fév. 2011) dans Org. Biomol. Chem.

"Allosterically driven self-assemblies of interlocked calix[6]arene receptors"

Le Gac, S.; Picron, J.-F.; Reinaud, O.; Jabin, I. Org. Biomol. Chem. 2011, 9, 2387-2396.

54- "Ru-TAP complexes with btz and pytz ligands: novel candidates as photooxidizing agents"

Mattiuzzi, A.; Jabin, I.; Moucheron, C.; Kirsch-De Mesmaeker, A. Dalton Trans. 2011, 40, 7395-

7402.

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55- "Structure-Activity Relationship Analyses of Glycyrrhetinic Acid Derivatives as Anticancer Agents"

Lallemand, B.; Gelbcke, M.; Dubois, J.; Prévost, M.; Jabin, I.; Kiss, R. Mini-Rev. Med. Chem. 2011,

11, 881-887.

56- "Second Generation Calix[6]trenamides: Highly Selective Graftable Receptors for Neutral Guests

and Contact Ion Pairs "

Lascaux, A.; Delahousse, G.; Ghostin, J.; Bouillon, J.-P.; Jabin, I. Eur. J. Org. Chem. 2011, 5272-5278.

57- Article sélectionné comme Hot Paper (Août 2011) dans Org. Biomol. Chem.

"Acid-base modulation of a versatile heteroditopic calix[6]arene based receptor"

Cornut, C.; Marrot, J.; Wouters, J.; Jabin, I. Org. Biomol. Chem. 2011, 9, 6373-6384.

58- "New structure activity relationship (SAR) of novel anticancer glycyrrhetinic acid derivatives"

Lallemand, B.; Gelbcke, M.; Dubois, J.; Jabin, I.; Kiss; R. Ann. Oncol. 2011, 22, 30.

59- "N-(2-{3-[3,5-bis(trifluoromethyl)phenyl]ureido}ethyl)-glycyrrhetinamide (6b): A Novel Anticancer

Glycyrrhetinic Acid Derivative that Targets the Proteasome and Displays Anti-Kinase Activity"

Lallemand, B.; Chaix, F.; Bury, M.; Bruyère, C.; Ghostin, J.; Becker, J.; Delporte, C.; Gelbcke, M.;

Mathieu, V.; Dubois, J.; Prévost, M.; Jabin, I.; Kiss, R. J. Med. Chem., 2011, 54, 6501-6513.

60- “Ipso-nitration of calix[6]azacryptands: intriguing effect of the small rim capping pattern on the

large rim substitution selectivity”

Lejeune, M.; Picron, J.-F.; Mattiuzzi, A.; Lascaux, A.; De Cesco, S.; Brugnara, A.; Thiabaud, G.;

Darbost, U.; Colasson, B.; Reinaud, O.; Jabin, I. J. Org. Chem., 2012, 77, 3838-3845.

61- “DYRK1A Kinase Inhibitors with Emphasis on Cancer”

Ionescu, A.; Dufrasne, F.; Gelbcke, M.; Jabin, I.; Kiss, R.; Lamoral-Theys, D. Mini-Rev. Med. Chem.

2012, 12, 1315-1329.

62- “Reductive electrografting of calix[4]arenediazonium salts onto surfaces: Anchoring versatile

platforms for spatially-controlled functionalization”

Mattiuzzi, A.; Jabin, I.; Mangeney, C.; Roux, C.; Reinaud, O.; Santos, L.; Bergamini, J.F.; Hapiot, P.;

Lagrost C. Nat. Commun. 2012, 3, 1130.

63- “Synthesis and Plasma Pharmacokinetics in CD-1 Mice of a 18β-glycyrrhetinic Acid Derivative

Displaying Anticancer Activity”

Lallemand, B.; Ouedraogo, M.; Wauthoz, N.; Lamkami, T.; Mathieu, V.; Jabin, I.; Amighi, K.; Kiss, R.;

Dubois, J.; Goole J. J. Pharm. Pharmacol. 2012, DOI: 10.1111/j.2042-7158.2012.01603.x.

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PUBLICATIONS G. EVANO

1- “Selective N-Dealkylation of Tertiary Amines Derived from Phenylglycinol or Ephedrine Family”

Agami, C.; Couty, F.; Evano, G. Tetrahedron Lett. 1999, 40, 3709-3712.

2- “Synthesis of -Substituted Allylic Amines via a Modified Bruylants Reaction”

Agami, C.; Couty, F.; Evano, G. Org. Lett. 2000, 2, 2085-2088.

3- “SN2’ Regio and Stereoselective Alkylation of Allylic and Propargylic Mesylates Linked to a N-Boc

Oxazolidine using Organocuprates”

Agami, C.; Couty, F.; Evano, G.; Mathieu, H. Tetrahedron, 2000, 56, 367-376.

4- “Claisen Rearrangement of Allylic Alcohols Prepared through N-Boc-2-acyloxazolidine

Methodology. Application to the Synthesis of Trisubstituted Cyclopropanes”

Agami, C.; Couty, F.; Evano, G. Tetrahedron Lett. 2000, 41, 8301-8305.

5- “Enantioselective Synthesis of 2-Substituted-N-Boc--4,5-piperidines”

Agami, C.; Couty, F.; Evano, G. Tetrahedron : Asymmetry, 2000, 11, 4639-4643.

6- “Claisen Rearrangement of Allylic and Propargylic Alcohols Prepared through N-Boc-2-

Acyloxazolidines Methodology. Application to the Synthesis of Original Chiral Building Blocks”

Agami, C.; Couty, F.; Evano, G. Eur. J. Org. Chem. 2002, 29-38.

7- “Some Uses of N-Boc-2-acyloxazolidines in Asymmetric Synthesis”

Couty, F.; Evano, G.; Matthieu, H.; Rabasso, N.; Venier, O. l'Actualité Chimique, 2002, 249, 13-18.

8- “A Straightforward Synthesis of Enantiopure 2-Cyanoazetidines from -Aminoalcohols”

Agami, C.; Couty, F.; Evano, G. Tetrahedron: Asymmetry 2002, 13, 297-302.

9- “Enantioselective Synthesis of Clavepictine analogues and Evaluation of their Cytotoxic Activity”

Agami, C.; Couty, F.; Evano, G.; Darro, F.; Kiss, R. Eur. J. Org. Chem. 2003, 2062-2070.

10- “Synthesis of enantiopure azetidine-2-carboxylic acids and their incorporation into peptides”

Couty, F.; Evano, G.; Rabasso, N. Tetrahedron: Asymmetry 2003, 14, 2407-2412.

11- “A Convergent Synthesis of the Macrocyclic Core of Cytotrienins: Application of RCM for

Macrocyclization”

Evano, G.; Schaus, J. V.; Panek, J. S. Org. Lett. 2004, 5, 525-528.

12- “Synthesis of Chiral Non Racemic Azetidines”

Couty, F.; Evano, G.; Prim, D. Minireviews in Organic Chemistry 2004, 1, 133-148.

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13- “Synthesis and Reactivity of Enantiomerically Pure N-Alkyl-2-alkenyl Azetidinium Salts”

Couty, F.; Durrat, F.; Evano, G.; Prim, D. Tetrahedron Lett. 2004, 45, 7525-7528.

14- “General Route to a New Class of Homochiral Azetidine-Derived 1,2-Diamines”

Couty, F.; Evano, G.; Prim, D.; Marrot, J. Eur. J. Org. Chem., 2004, 3893-3897.

15- “N-Cyanomethyl--chloroamines: A Convenient Source of Aziridinium Ions”

Couty, F.; Evano, G.; Prim, D. Tetrahedron Lett. 2005, 46, 2253-2257.

16- “Azetidine motifs as ligand in the Pd(II) complexes series”

Keller, L.; Vargas Sanchez, M.; Prim, D.; Couty, F.; Evano, G.; Marrot, J. J. Organomet. Chem. 2005,

690, 2306-2311.

17- “Regioselective Nucleophilic Opening of Azetidinium Ions”

Couty, F.; Durrat, F.; Evano, G. Synlett 2005, 1666-1670.

18- “Azetidinic Amino Acids: Stereocontrolled Synthesis and Pharmacological Characterization as

Ligands for the Glutamate Receptors and Transporters”

Bräuner-Osborne, H.; Bunch, L. Chopin, N., Couty, F.; Evano, G.; Jensen, A. A.; Kusk, M.; Nielsen,

B.; Rabasso, N. Org. Biomol. Chem. 2005, 3926-3936.

19- “Practical Asymmetric Preparation of Azetidine-2-carboxylic Acid”

Couty, F.; Evano, G.; Vargas-Sanchez, M.; Bouzas, G. J. Org. Chem., 2005, 70, 9028-9031.

20- “Total Synthesis of Reblastatin”

Wrona, I.; Gabarda, A.; Evano, G.; Panek, J. S. J. Am. Chem. Soc., 2005, 127, 15026-15027 (repris

dans Synfacts, 2006, 312).

21- “3-Aminopyrrolidines via Ring Rearrangement of 2-Aminomethylazetidines. Synthesis of (-)-

Absouline”

Vargas-Sanchez, M.; Couty, F.; Evano, G.; Prim, D.; Marrot, J. Org. Lett. 2005, 6, 5861-5864.

22- “Stereocontrolled Synthesis of 3-Substituted Azetidinic Amino Acids”

Sivaprakasam, M.; Couty, F.; Evano, G.; Srinivas, B.; Sridhar, R.; Rama Rao, K. Synlett 2006, 781-

785.

23- “N-Cyanomethyl--chloro amines: chiral building blocks for the synthesis of azacrown ethers”

Couty, F.; Evano, G.; Menguy, L.; Steimetz, V.; Toumi, M. Tetrahedron Lett. 2006, 47, 4817-4821.

24- “Nucleophilic Ring-Opening of Azetidinium Ions: Insights into Regioselectivity”

Couty, F.; David, O.; Durrat, F.; Evano, G.; Lakhdar, S.; Marrot, J.; Vargas-Sanchez, M. Eur. J. Org.

Chem. 2006, 3479-3490.

25- “Ring Expansions of 2-Alkenylazetidinium Salts – a New Route to Pyrrolidines and Azepanes”

Couty, F.; Durrat, F.; Evano, G.; Marrot, J. Eur. J. Org. Chem. 2006, 4214-4223.

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26- “Azetidine-2-Carboxylic Acid. From Lily of the Valley to Key Pharmaceuticals. A Jubilee Review”

Couty, F.; Evano, G. Org. Prep. Proced. Int. 2006, 38, 427-465.

27- “The Reaction of Azetidines with Chloroformates”

Vargas-Sanchez, M.; Lakhdar, S.; Couty, F.; Evano, G. Org. Lett. 2006, 8, 5501-5504.

28- Article faisant la couverture d’Angew. Chem. Int. Ed. :

“Total Synthesis of Paliurine F”

Toumi, M.; Couty, F.; Evano, G. Angew. Chem. Int. Ed. 2007, 46, 572-575 (repris dans Synfacts,

2007, 571).

29- “A Straighforward Synthesis of 3-Substituted Azetidinic Amino Acids”

Sivaprakasam, M.; Couty, F.; Evano, G.; Srinivas, B.; Sridhar, R.; Rama Rao, K. Arkivoc, 2007, Part

(x): Commemorative Issue in Honor of Prof. Alain Krief on the occasion of his 65th Anniversary,

71-93.

30- Article faisant la couverture du J. Org. Chem. :

“Total Synthesis of the Cyclopeptide Alkaloid Abyssenine A. Application of Inter- and

Intramolecular Copper-Mediated Coupling Reactions in Organic Synthesis”

Toumi, M.; Couty, F.; Evano, G. J. Org. Chem., 2007, 72, 9003-9009 (repris dans Synfacts, 2008,

338).

31- “Eight Steps Total Synthesis of the Cyclopeptide Alkaloid Mucronine E”

Toumi, M.; Couty, F.; Evano, G. Synlett, 2008, 29-32.

32- “A Practical Route to Enantiopure 3-Hydroxy-pyrrolidines: Application to a Straightforward

Synthesis of (-)-Bulgecinine”

Toumi, M.; Couty, F.; Evano, G. Tetrahedron Lett. 2008, 49, 1175-1179.

33- “Total Synthesis of the Cyclopeptide Alkaloid Paliurine E. Insights into Macrocyclization by Ene-

enamide RCM”

Toumi, M.; Couty, F.; Evano, G. J. Org. Chem. 2008, 73, 1270-1281.

34- “Rearrangement of 2-Hydroxyalkylazetidines into 3-Fluoropyrrolidines”

Drouillat, B.; Couty, F.; David, O.; Evano, G.; Marrot, J. Synlett 2008, 1345-1348.

35- “Ring Expansion of 2-(α-Hydroxyalkyl)azetidines: A Synthetic Route to Functionalized Pyrrolidines”

Durrat, F.; Vargas-Sanchez, M.; Couty, F.; Evano, G.; Marrot, J. Eur. J. Org. Chem. 2008, 3286-

3297.

36- “Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed

Biomolecules Synthesis”

Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054-3131.

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37- “Des Acides Aminés et du Cuivre(I) pour la Synthèse d’Alcaloïdes Cyclopeptidiques”

Evano, G. l'Actualité Chimique, 2008, 322, 20-26.

38- “Copper-Catalyzed Cyclization of Iodo-tryptophans: A Straightforward Synthesis of Pyrroloindoles”

Coste, A.; Toumi, M.; Wright, K.; Razafimahaléo, V.; Couty, F.; Marrot, J.; Evano, G. Org. Lett.

2008, 10, 3841-3844.

39- “Total Synthesis of Chaetominine”

Toumi, M.; Couty, F.; Marrot, J.; Evano, G. Org. Lett. 2008, 10, 5027-5030.

40- “TMC-95A-D: Chemistry and Biology”

Coste, A.; Couty, F.; Evano, G. C. R. Chimie 2008, 11, 1544-1573, Numéro spécial “Natural

Products with Anticancer Properties”.

41- “Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen Nucleophiles: A General

Method for the Synthesis of Ynamides”

Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew. Chem. Int. Ed. 2009, 48, 4381-4385 (repris

dans Synfacts, 2009, 907).

42- “Copper-Catalyzed Cyclization Reactions for the Synthesis of Alkaloids”

Evano, G.; Toumi, M. Coste, A. Chem. Commun. 2009, 4166-4175.

43- “A General Route to Cyclopeptide Alkaloids: Total Syntheses and Biological Evaluation of

Paliurines E and F, Ziziphines N and Q, Abyssenine A, Mucronine E, and Analogues”

Toumi, M.; Rincheval, V.; Young, A.; Gergeres, D.; Turos, E.; Couty, F.; Mignotte, B.; Evano, G. Eur.

J. Org. Chem. 2009, 3368-3386.

44- “Second-Generation, Biomimetic Total Synthesis of Chaetominine”

Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Synthesis 2009, 2927-2934, Numéro spécial

“Natural Product Synthesis”.

45- “Synthesis of Ketene N,N-Acetals by Copper-Catalyzed Double-Amidation of 1,1-Dibromo-1-

alkenes”

Coste, A.; Couty, F.; Evano, G. Org. Lett. 2009, 11, 4454-4457.

46- “Azetidines: New Tools for the Synthesis of Nitrogen Heterocycles”

Couty, F.; Evano, G. Synlett 2009, 3053-3064.

47- “Ynamides: Versatile Tools in Organic Synthesis”

Evano, G.; Coste, A.; Jouvin, K. Angew. Chem. Int. Ed. 2010, 49, 2840-2859.

48- “Copper-Mediated Homocoupling of Vinyl Dibromides to Symmetrical Diynes”

Coste, A.; Couty, F. Evano, G. Synthesis 2010, 1500-1504.

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49- “Synthesis of the Azetidinyl-Thiazoline Fragment of Vioprolides A and C”

Chopin, N.; Couty, F.; Evano, G. Lett. Org. Chem. 2010, 7, 353-359.

50- “Synthesis of Ynamides by Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen

Nucleophiles. Preparation of N-Benzyl-N-4-toluenesulfonyl-phenylethynylamine”

Coste, A.; Couty, F.; Evano, G. Org. Synth. 2010, 87, 231-244.

51- “Copper-Catalyzed Alkynylation of Amides with Potassium Alkynyltrifluoroborates: A Room-

Temperature, Base-Free Synthesis of Ynamides”

Jouvin, K.; Couty, F.; Evano, G. Org. Lett. 2010, 12, 3272-3275.

52- “Organic Azides – Syntheses and Applications. By S. Bräse and K. Banert”

Evano, G. Angew. Chem. Int. Ed. 2010, 49, 6025.

53- “Vinyl Dibromides: Versatile Partners in Cross-Coupling Reactions”

Legrand, F.; Jouvin, K. Evano, G. Isr. J. Chem. 2010, 50, 588-604. Numéro spécial “Metal-Catalyzed

Cross-Coupling Reactions”.

54- “Copper-Mediated Cross-Coupling of 1,1-Dibromo-1-alkenes with Dialkylphosphites: a Convenient

Synthesis of 1-Alkenylphosphonates”

Evano, G.; Tadiparthi, K.; Couty, F. Chem. Comm. 2011, 47, 179-181. Numéro spécial “Emerging

Investigators”.

55- “Highly Regio- and Stereo- selective Nickel-Catalyzed Addition of Dialkylphosphites to Ynamides:

an Efficient Synthesis of -Amino Vinylphosphonates”

Fadel, A.; Legrand, F.; Evano, G.; Rabasso, N. Adv. Synth. Catal. 2011, 353, 263-267.

56- “Copper-Catalysed N-Alkynylation of Benzimidazoles and Indazoles”

Jouvin, K.; Evano, G. Chimica Oggi-Chemistry Today 2011, 29, 31-33.

57- “Copper-Catalyzed Oxidative Alkynylation of Diaryl Imines with Terminal Alkynes: A Facile

Synthesis of Ynimines”

Laouiti, A.; Rammah, M. M.; Rammah, M. B.; Marrot, J.; Couty, F.; Evano, G. Org. Lett. 2012, 14,

6-9.

58- “Click-Alkynylation of N- and P-Nucleophiles by Oxidative Cross-Coupling with Alkynylcopper

Reagents: a General Synthesis of Ynamides and Alkynylphosphonates”

Jouvin, K.; Heimburger, J.; Evano, G. Chem. Sci. 2012, 3, 756-760.

59- “Copper-Catalyzed Coupling of 1,1-Dibromo-1-alkenes with Phenols: A General, Modular, and

Efficient Synthesis of Ynol Ethers, Bromo Enol Ethers, and Ketene Acetals”

Jouvin, K.; Bayle, A.; Legrand, F.; Evano, G. Org. Lett. 2012, 14, 1652-1655.

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60- “Oxidative Alkynylation of Imines with Alkynylcopper Reagents: A Straightforward and Practical

Entry to Ynimines”

Laouiti, A.; Jouvin, K.; Rammah, M. M.; Rammah, M. B.; Evano, G. Synthesis 2012, 44, 1491-1500.

Numéro spécial “Copper in Organic Synthesis”.

61- “Stereoselective Hydrofluorination of Ynamides: a Straightforward Synthesis of Novel α-

Fluoroenamides”

Compain, G.; Jouvin, K.; Martin-Mingot, A.; Evano, G.; Marrot, J.; Thibaudeau, S. Chem. Commun.

2012, 48, 5196-5198.

62- “De Novo Synthesis of 1,4-Dihydropyridines and Pyridines”

Gati, W.; Rammah, M. M.; Rammah, M. B.; Couty, F.; Evano, G. J. Am. Chem. Soc. 2012, 134,

9078-9081 (repris dans Synfacts, 2012, 8, 900).

63- “Copper-Mediated Selective Cross-Coupling of 1,1-Dibromo-1-alkenes and Heteronucleophiles:

Development of General Routes to Heterosubtituted Alkynes and Alkenes”

Jouvin, K.; Coste, A.; Bayle, A.; Legrand, F.; Karthikeyan, G.; Tadiparthi, K.; Evano, G.

Organometallics 2012, 31, 7933-7947. Numéro spécial "Copper Organometallic Chemistry".

64- “Intramolecular Carbolithiation of N-Allyl-ynamides: an Efficient Entry to 1,4-Dihydropyridines and

Pyridines - Application to a Formal Synthesis of Sarizotan”

Gati, W.; Rammah, M. M.; Rammah, M. B.; Evano, G. Beilstein J. Org. Chem. 2012, 8, 2214-2222.

Série thématique "Carbometallation Chemistry".

65- “General Amination Reactions for the Synthesis of Ynamides”

Evano, G.; Jouvin, K.; Coste, A. Synthesis 2013, 45, 17-26.

66- “Expanding the Oxidative Chemistry of Organocopper Reagents: Facile Oxidative Cross-Coupling

of Copper Acetylides with Arylboronic Acids”

Verna, F.; Guissart, C.; Pous, J.; Evano, G. Monatsh. Chem. 2013, sous presse, DOI :

10.1007/s00706-012-0896-0. Numéro spécial "Young Investigators"