Wittig Olefination–Claisen Rearrangement Protocol for Cyclohexene Annulation

Abstract

A two-step iterative sequence of Wittig olefination followed by Claisen rearrangement resulted in 1,7-octadienes, which afforded the corresponding cyclohexene carbaldehydes upon ring-closing metathesis with Grubbs catalyst.

Keywords:

• Claisen rearrangement
• cyclohexene annulation
• ring-closing metathesis
• Wittig olefination

ACKNOWLEDGMENTS

D. D. G., A. S. B., Y. B. S., V. B. N., S. W. C., A. P. D., M. P. D., and D. R. B. thank the Council of Scientific and Industrial Research, New Delhi, India, for the fellowships.

Notes

^a Yield is calculated on the basis of recovered starting material; Z/E geometrical and diastereomeric ratios were obtained from the NMR.