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A metal-catalyzed new approach for α-alkynylation of cyclic amines
Yifan Cui1,2, Weilong Lin1,2, Shengming Ma1,3
1State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , P. R. China .
Abstract:
The first catalytic α-alkynylation of cyclic amines with the help of the N-propargylic group to afford 2-(1-alkynyl) N-allylic cyclic amines with an exclusive E-stereoselectivity for the in situ formed C[double bond, length as m-dash]C bond has been realized. Based on mechanistic studies, it is proven that the reaction proceeds through metal-mediated anti-1,5-hydride transfer forming an iminonium intermediate, which accepts the addition of the in situ generated 1-alkynyl metal species. The synthetic application has also been demonstrated.
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