Issue 23, 2020

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 terms of 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 catalysed by chiral Brønsted acids with 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 acids via a concerted hydroamination mechanism.

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2020,11, 5987-5993

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, 11, 5987 DOI: 10.1039/D0SC00001A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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