Highly enantioselective catalytic cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinolines and terminal alkynes

Organic Letters
Shutao SunLei Liu

Abstract

The first catalytic asymmetric cross-dehydrogenative coupling of cyclic carbamates and terminal alkynes has been established. The reaction features high enantiocontrol and excellent functional group tolerance and displays a wide range of structurally and electronically diverse carbamates as well as terminal alkynes. N-Acyl hemiaminals were identified as the reactive intermediates through preliminary control experiments. Employing readily removable carbamates as substrates rather than traditionally adopted N-aryl amines allows applications in complex molecule synthesis and therefore advances the C-H functionalization strategy to a synthetically useful level.

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Citations

Sep 4, 2015·Organic Letters·Bérénice C Lemercier, Joshua G Pierce
Nov 13, 2015·Organic Letters·Changcun YanQingmin Wang
Apr 15, 2016·Journal of Medicinal Chemistry·Hongbo ZhengHongxiang Lou
Sep 30, 2016·Chemical Reviews·Maria ChrzanowskaMaria D Rozwadowska
Oct 16, 2015·Organic & Biomolecular Chemistry·Jiayu ChenLei Liu
May 22, 2018·Organic & Biomolecular Chemistry·Longyang DianYunfei Du
Jun 26, 2018·Organic & Biomolecular Chemistry·Yuanyuan WeiCongde Huo
Nov 12, 2019·Organic & Biomolecular Chemistry·Shikha Gandhi
Feb 16, 2016·Beilstein Journal of Organic Chemistry·Jixin LiuMary P Watson

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