Issue 6, 2018, Issue in Progress
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RSC Advances

Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction†‡

Cheng-Ke Tang, ORCID logo a   Kai-Xiang Feng,a   Ai-Bao Xia, ORCID logo *a   Chen Li,a   Ya-Yun Zheng,a   Zhen-Yuan Xua  and  Dan-Qian Xu*a  

* Corresponding authors

a Catalytic Hydrogenation Research Centre, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, China
E-mail: xiaaibao@zjut.edu.cn, chrc@zjut.edu.cn

Abstract

A catalytic asymmetric method for the synthesis of polysubstituted chromans via an oxa-Michael-nitro-Michael reaction has been developed. The squaramide-catalyzed domino reaction of 2-hydroxynitrostyrenes with trans-β-nitroolefins produced chiral chromans with excellent enantioselectivities (up to 99% ee), diastereoselectivities (up to >20 : 1 dr), and moderate to good yields (up to 82%).

Graphical abstract: Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction

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Article information

DOI
https://doi.org/10.1039/C7RA13525D
Article type
Paper
Submitted
21 Dec 2017
Accepted
28 Dec 2017
First published
17 Jan 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 3095-3098

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Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction

C. Tang, K. Feng, A. Xia, C. Li, Y. Zheng, Z. Xu and D. Xu, RSC Adv., 2018, 8, 3095 DOI: 10.1039/C7RA13525D

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