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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.

SUBMITTER: Fleming MJ

PROVIDER: S-EPMC8450947 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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

Fleming Matthew J MJ Hodgson David M DM

Beilstein journal of organic chemistry 20210910

α-Lithiated terminal epoxides and <i>N</i>-(<i>tert</i>-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. ...[more]

PMID: 34621400

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