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Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction Kiran Indukuri, Somasekhar Bondalapati, Sabera Sultana and Anil K. Saikia* S1 Electronic Supplementary Material (ESI) for RSC Advances This journal is © The Royal Society of Chemistry 2012

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Page 1: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

Supplementary Information

Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

Kiran Indukuri, Somasekhar Bondalapati, Sabera Sultana and Anil K. Saikia*

S1

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 2: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

Experimental Section

General

All the reagents are commercially obtained. BF3·Et2O was distilled over CaH2 prior to use.1H NMR spectra were recorded in CDCl3 on Varian AS 400 (400 MHz) spectrometer using TMS as internal standard. The 13C spectra were obtained on Varian AS 400 operating at 100 MHz. IR spectra were recorded on Nicolet Impact 410 FT-IR spectrometer. HRMS spectra were recorded using ESI mode. Melting points were measured in open capillary tubes and are uncorrected. All 3-ethoxy cyclobutanones are prepared by the following literature methods. Ref: 1) J.-i. Matsuo, R. Okuno, K. Takeuchi, M. Kawano and H. Ishibashi, Tetrahedron Lett. 2010, 51, 3736. 2) J.-i. Matsuo, S. Sasaki, H. Tanaka and H. Ishibashi, J. Am. Chem. Soc. 2008, 130, 11600.

S2

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 3: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 1

S3

OO

OO

cis:trans=1:8

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 4: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 1

 

S4

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 5: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 2

 

S5

OO

OO

cis:trans=1:8

Br

Br

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 6: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 2

 

S6

OO

Br

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 7: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 3

 

S7

OO

OO

cis:trans=1:9

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 8: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 3

 

S8

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 9: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 4

 

S9

OO

OO

cis:trans=1:8

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 10: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 4

 

S10

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 11: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 5

 

S11

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 12: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 5

 

S12

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 13: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 6

 

S13

OO

Cl

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 14: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 6

 

S14

OO

Cl

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 15: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 7

 

S15

OO

PhPh

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 16: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 7

 

S16

OO

PhPh

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 17: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 8

 

S17

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 18: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 8

                   

S18

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 19: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 9

 

S19

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 20: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 9

 

S20

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 21: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 10

 

S21

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 22: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 10

S22

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 23: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 13

 

S23

OO

OO

cis:trans=1:17

Ph

Ph

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 24: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 13

 

S24

OO

Ph

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 25: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 14

 

S25

OO

OO

cis:trans=1:12

Ph

PhMe

Me

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 26: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 14

 

S26

OO

PhMe

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 27: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 15

 

S27

OO

OO

cis:trans=1:8

Ph

Ph

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 28: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 15

 

S28

OO

Ph

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 29: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 16

 

S29

OO

Br

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 30: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 16

 

S30

OO

Br

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 31: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 17 

 

S31 

OO

OO

cis:trans=1:5

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 32: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 17

 

 

S32 

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 33: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

1H NMR spectrum of 18 

 

 

S33

cis:trans=1 :7

OO

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 34: Supplementary Information Synthesis of 2,3-Dihydro-4 ... · Supplementary Information Synthesis of 2,3-Dihydro-4-pyranones from Epoxides via Intermolecular [4+2] Cycloaddition Reaction

 

 

13C NMR spectrum of 18 

 

S34

OO

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012


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