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

alpha-Lithiated terminal epoxides and N-(tert-butylsulfonyl)aziridines undergo eliminative cross-coupling with alpha-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 beta-elimination of lithium alkoxide.

Automated summary

The reaction involves the cross-coupling of alpha-lithiated terminal epoxides and N-(tert-butylsulfonyl)aziridines with alpha-lithio ethers to yield allylic alcohols and allylic amines. The mechanism proceeds through selective strain-relieving attack and beta-elimination of the lithium alkoxide.