Page 1
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
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
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
13C NMR spectrum of 1
S4
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 5
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
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
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
13C NMR spectrum of 3
S8
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 9
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
13C NMR spectrum of 4
S10
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 11
1H NMR spectrum of 5
S11
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 12
13C NMR spectrum of 5
S12
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 13
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
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
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
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
1H NMR spectrum of 8
S17
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 18
13C NMR spectrum of 8
S18
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 19
1H NMR spectrum of 9
S19
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 20
13C NMR spectrum of 9
S20
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 21
1H NMR spectrum of 10
S21
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 22
13C NMR spectrum of 10
S22
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 23
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
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
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
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
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
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
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
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
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
13C NMR spectrum of 17
S32
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012
Page 33
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
13C NMR spectrum of 18
S34
OO
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012