Issue 63, 2020, Issue in Progress
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RSC Advances

Highly enantioselective copper-catalyzed propargylic amination to access N-tethered 1,6-enynes†

Si-Jia Li,‡a   Jian Huang,‡a   Jin-Yu He,a   Rui-Jin Zhang,a   Hao-Dong Qian,a   Xue-Lin Dai,a   Han-Han Konga  and  Hao Xu ORCID logo *a  

* Corresponding authors

a CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides & Chemical Biology Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China
E-mail: hao.xu@ccnu.edu.cn

Abstract

A highly enantioselective copper-catalyzed propargylic amination starting from benzylic allylic amines has been developed with a new chiral N,N,P ligand. A series of N-tethered 1,6-enynes were synthesized in good to excellent yields with excellent enantioselectivities. Utilization of transition metal-catalyzed cycloisomerization of 1,6-enynes provides several enantioselectively enriched chiral five-membered N-heterocycles efficiently.

Graphical abstract: Highly enantioselective copper-catalyzed propargylic amination to access N-tethered 1,6-enynes

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Article information

DOI
https://doi.org/10.1039/D0RA07698H
Article type
Paper
Submitted
08 Sep 2020
Accepted
12 Oct 2020
First published
20 Oct 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 38478-38483

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Highly enantioselective copper-catalyzed propargylic amination to access N-tethered 1,6-enynes

S. Li, J. Huang, J. He, R. Zhang, H. Qian, X. Dai, H. Kong and H. Xu, RSC Adv., 2020, 10, 38478 DOI: 10.1039/D0RA07698H

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