Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines

Abstract

α-Lithiated terminal epoxides and N-(tert-butylsulfonyl)aziridines undergo eliminative cross-coupling with α-lithio ethers, to give convergent access to allylic alcohols and allylic amines, respectively. The process can be considered as proceeding by selective strain-relieving attack (ring-opening) of the lithiated three-membered heterocycle by the lithio ether and then selective β-elimination of lithium alkoxide.

Keywords: alkenes; aziridines; epoxides; lithiation; synthetic methods.