Site and Stereoselectivity of the Cyclopropanation of Unsymmetrically Substituted 1,3-Dienes by the Simmonssmith Reaction.⁺

⁺Part of the results was presented at the XVIth International Conference on Organometallic Chemistry, Brighton, July 1994, abstract P228.

Abstract

In the Simmons-Smith reaction, 1,3-dienes are preferentially cyclopropanated at the more electron-rich double bond to afford the trans-vinylcyclopropane; an allylic hydroxyl group increases the reactivity and directs the cyclopropanation to the adjacent double bond.

⁺Part of the results was presented at the XVIth International Conference on Organometallic Chemistry, Brighton, July 1994, abstract P228.

Notes

⁺Part of the results was presented at the XVIth International Conference on Organometallic Chemistry, Brighton, July 1994, abstract P228.