one- and two –component domino reactionsgbdong.cm.utexas.edu/seminar/2015/2015-04-15.pdf ·...
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One- and Two –Component Domino
reactions
Dong group at UT Austin
Xuan Zhou
04/15/2015
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Chem. Rev. 2013, 113, 442–5242
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One- and Two –Component Domino reactions
ContentA, Anionic primary step
B, Cationic sequence
C, Initiated by a pericyclic primary step
D, Carbene sequence
E, Palladium catalyzed domino reaction
F, Ruthenium catalyzed domino reaction
G, Miscellaneous domino reactions
Reviews about domino reactions:
Chem. Rev. 2014, 114, 2390; Chem. Rev. 2014, 114, 8323; Green Chem. 2014, 16, 2958;
Chem. Soc. Rev. 2014, 43, 4368; Tetrahedron 2013, 69, 7171; Chem. Soc. Rev. 2013, 42, 4948
Domino reaction: two or more bond-forming in one reaction vessel, and no
additional reagents, catalysts, or additives can be added during the reaction.
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Synthesis of Salvinorin A through Domino Michael/Michael Reaction
Evans, D. A. J. Am. Chem. Soc. 2007, 129, 8968.
Anionic primary step
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Anionic primary step
Synthesis of (-)-Chokol A through Domino Michael/Dieckmann Reaction
Kreye, P. Synlett 2006, 22235
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Anionic primary step
Synthesis of Key Intermediate in the Synthesis of Himbacine
through Domino Michael/Dieckmann Reaction
McCarthy, R. Synlett 2011, 8016
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Anionic primary step
Csaky, A. G. Org. Lett. 2012, 14, 1187
Domino Michael/Acetal Ring-Opening Reaction
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Anionic primary stepIntra- and Intermolecular Domino Michael/
Ylide Epoxidation Reactions
Tang, Y. J. Am. Chem. Soc. 2008, 130, 54088
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Anionic primary step
Tang, Y. J. Org. Chem. 2010, 75, 3454
Domino Michael/Ylide
Cyclopropanation Reaction
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Domino Michael/Wittig Reaction
Anionic primary step
Zhou, Y.-G. Chem. Commun. 2009, 309210
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Anionic primary step
Synthesis of Oseltamivir through Domino Michael/Horner-
Wadsworth-Emmons Reaction
Lu, G. J. Org. Chem. 2010, 75, 312511
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Anionic primary step
Synthesis of ABT-341 through Domino Michael/
Horner-Wadsworth-Emmons Reaction
Hayashi, Y. Angew. Chem., Int. Ed. 2011, 50, 282412
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Anionic primary step
Davies, S. G. Tetrahedron: Asymmetry 2006, 17, 2183
Synthesis of Precursor of (-)-Pumiliotoxin C through
Domino Aza-Michael/Michael Reaction
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Anionic primary step
Domino Thia-Michael/Aldol Reaction of Chiral 3-
Cinnamoyloxazolidine-2-thione with Aromatic Aldehydes
Tanabe, G. Chem.—Eur. J. 2006, 12, 389614
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Intramolecular Domino Hetero-Michael/Mannich-type Reaction
Nagasaka, T. Tetrahedron: Asymmetry 2007, 18, 153316
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Domino Imino-Aldol/Aza-Michael Reaction
Anionic primary step
Das, R. K. J. Org. Chem. 2010, 75, 706117
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Domino Imino-Aldol/Aza-Michael Reaction
Das, R. K. J. Org. Chem. 2010, 75, 706118
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Synthesis of (-)-PNU-286607 through Domino
Knoevenagel/[1,5]-Hydrogen Shift/Cyclization Reaction
Anionic primary step
Kamilar, G. M. J. Am. Chem. Soc. 2009, 131, 399119
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Synthesis of (+)-Chinensiolide B through Domino
Allylboration/Lactonization Reaction
Hall, D. G. J. Am. Chem. Soc. 2010, 132, 148820
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Synthesis of Alkaloids through Domino Horner-Wadsworth-
Emmons/Isomerization/Claisen Rearrangement Reaction
Kawasaki, T. J. Org. Chem. 2010, 75, 112621
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Domino Amidation/Cyclization Reaction Followed by
Intramolecular Electrophilic Aromatic Substitution
Stalke, D. Org. Lett. 2009, 11, 523022
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Domino Ethanolysis/Dehydrobromation/
Aziridination Reaction
Fukuyama, T. Tetrahedron 2009, 65, 323923
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Domino SN2/Michael Reactions
Reddy, S. R. B. Org. Lett. 2009, 11, 251924
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Domino Intramolecular Azetidine
RingOpening/Closing Reaction
Compain, P. Eur. J. Org. Chem. 2011, 661925
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Domino Elimination/1,6-Addition Reaction
Metz, P. Chem.—Eur. J. 2011, 17, 1333426
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Cationic sequence
Synthesis of (-)-Dysibetaine PP through
Domino Cyclization Reaction
Blaauw, R. H. Org. Lett. 2006, 8, 23927
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Synthesis of Schweinfurthin G through Domino
Epoxide-Opening/Cyclization Reaction
Cationic sequence
Wiemer, D. F. J. Org. Chem. 2008, 73, 796328
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Synthesis of (+)-Stachyflin through Domino Epoxide-
Opening/Rearrangement/Cyclization Reaction
Cationic sequence
Katoh, T. Chem. Commun. 2010, 46, 405529
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Domino Prins/Friedel-Crafts Reaction
Cationic sequence
Aub’e, J. Org. Lett. 2011, 13, 261430
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Oxidative Domino Prins/Pinacol Reaction
Cationic sequence
Canesi, S. J. Org. Chem. 2011, 76, 946031
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Initiated by a pericyclic primary step
Domino Intramolecular Diels-Alder Cycloaddition/1,3-
Dipolar Cycloaddition Reaction
Boger, D. L. J. Am. Chem. Soc. 2010, 132, 1353332
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Initiated by a pericyclic primary step
Domino Intramolecular Ynamide
Benzannulation Reaction
Danheiser, R. L. J. Org. Chem. 2011, 76, 1852.33
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Domino Oxy-Cope/Claisen/Ene Reaction
Initiated by a pericyclic primary step
Barriault .J. Am. Chem. Soc. 2007, 129, 211234
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Domino Retro-Diels-Alder Cycloaddition/
Diels-Alder Cycloaddition Reactions
Initiated by a pericyclic primary step
Porco, J. A., Jr. J. Org. Chem. 2011, 76, 894435
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Carbene sequence
Domino Carbonyl Ylide Formation/1,3-
Dipolar Cycloaddition Reaction
Hashimoto, S. Chem.—Eur. J. 2006, 12, 889836
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Carbene sequence
Domino Carbonyl Ylide Formation/1,3-Dipolar
Cycloaddition Reaction
Schaus, S. E. J. Org. Chem. 2007, 72, 9998 37
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Carbene sequence
Domino Carbonyl Ylide Formation/1,3-Dipolar Cycloaddition Reaction
and Total Synthesis of Pseudolaric Acid A
Chiu, P. Angew. Chem., Int. Ed. 2006, 45, 619738
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Palladium catalyzed domino reaction
Domino Carbopalladation/Heck Reaction and Domino
Carbopalladation/Stille Reaction
Herbst-Immer, R. J. Am. Chem. Soc. 2009, 131, 17879 39
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Palladium catalyzed domino reaction
Domino Heck/Lactonization Reaction
Domino Heck/Aza-Michael Reaction
Roy, R. J. Org. Chem. 2009, 74, 8480
Pfeffer, F. M. Tetrahedron Lett. 2012, 53, 1468 40
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Palladium catalyzed domino reaction
Domino Wacker/Heck Reaction
Gouverneur, V. J. Org. Chem. 2006, 71, 839041
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Palladium catalyzed domino reaction
Syntheses of (+)-Lysergic Acid, (+)-Lysergol, and (+)-
Isolysergol through Domino Cyclization Reaction
Ohno, H. J. Org. Chem. 2011, 76, 207242
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Palladium catalyzed domino reaction
Domino Oxa-Michael/Tsuji-Trost Reaction
Menche, D. Angew. Chem., Int. Ed. 2010, 49, 927043
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Ruthenium catalyzed domino reaction
Domino Olefin Cross-Metathesis/Intramolecular Aza-Michael Reaction
Domino Olefin Cross-Metathesis/Intramolecular Oxa-Michael Reaction
Pozo, C. J. Am. Chem. Soc. 2007, 129, 6700
Sasaki, M. Org. Lett. 2010, 12, 163644
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Ruthenium catalyzed domino reaction
Domino Ring-Opening/Ring-Closing Metathesis Reactions
Phillips, A. J. Angew. Chem., Int. Ed. 2008, 47, 849945
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Ruthenium catalyzed domino reaction
Domino Ring-Opening/Ring-Closing Metathesis Reactions
Phillips, A. J. Angew. Chem., Int. Ed. 2009, 48, 2346
Ghosh, S. Tetrahedron Lett. 2010, 51, 275446
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Ruthenium catalyzed domino reaction
Synthesis of Kempene-2, Kempene-1, and 3-epi-Kempene-1
through Domino Enyne Metathesis Reaction
Metz, P. Angew. Chem., Int. Ed. 2011, 50, 295447
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Miscellaneous domino reactions
Domino 1,3-Migration/[2 + 2]-Cycloaddition Reaction
Chan, P. W. H. J. Am. Chem. Soc. 2011, 133, 1524848
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Miscellaneous domino reactions
Domino Oxidation/Intramolecular Hetero-Diels-Alder Cycloaddition Reaction
Arseniyadis, S.Org. Lett. 2007, 9, 1351 49
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Miscellaneous domino reactions
Domino Epoxide-Opening/Oxidative Cleavage/Cyclization Reaction
Kita, Y. Chem.—Eur. J. 2007, 13, 523850
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Synthesis of Hirsutellone B through Al-Catalyzed
Domino Epoxide-Opening/Diels-Alder Reaction
Miscellaneous domino reactions
Nicolaou, K. C.; Sarlah, D.; Wu, T. R.; Zhan, W. Angew. Chem., Int. Ed. 2009, 121, 7002.51
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Miscellaneous domino reactions
Domino 1,3-H-1,7-H Shift/6π Electron Pericyclic Ring-
Closure/[4 + 2]-Cycloaddition Reaction
Hsung, R. P. Org. Lett. 2010, 12, 115252
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Palladium catalyzed domino reaction
Synthesis of 1α,25-Dihydroxyvitamin D3 through
Domino Cyclization/Suzuki Coupling Reaction
Mourino, A. Chem.—Eur. J. 2010, 16, 143254
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Miscellaneous domino reactions
Domino bromination/Cyclization Reactions
Herranz, R. J. Org. Chem. 2007, 72, 539555
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