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Desymmetrization of unactivated bis-alkenes via chiral Brønsted acid-catalysed hydroamination

Abstract

Although great success has been achieved in catalytic asymmetric hydroamination of unactivated alkenes using transition metal catalysis and organocatalysis, the development of catalytic desymmetrising hydroamination of such alkenes remains a tough challenge in attaining a high level of stereocontrol over both remote sites and reaction centers at the same time. To address this problem, here we report a highly efficient and practical desymmetrising hydroamination of unactivated alkenes catalyzed by chiral Brønsted acid in both high diastereoselectivity and enantioselectivity. This method features a remarkably broad alkene scope, ranging from mono-substituted and gem-/1,2-disubstituted to the challenging tri- and tetra-substituted alkenes, to provide access to a variety of diversely functionalized chiral pyrrolidines bearing two congested tertiary or quaternary stereocenters with excellent efficiency under mild and user-friendly synthetic conditions. The key to success is indirect activation of unactivated alkenes by chiral Brønsted acid via a concerted hydroamination mechanism.

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Supplementary files

Article information


Submitted
01 Jan 2020
Accepted
19 May 2020
First published
20 May 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Accepted Manuscript
Article type
Edge Article

Desymmetrization of unactivated bis-alkenes via chiral Brønsted acid-catalysed hydroamination

Z. Yu, Y. Cheng, N. Jiang, J. Wang, L. Fan, Y. Yuan, Z. Li, Q. Gu and X. Liu, Chem. Sci., 2020, Accepted Manuscript , DOI: 10.1039/D0SC00001A

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