Issue 38, 2013
From the journal:

RSC Advances

Highly enantioselective direct vinylogous Michael addition of γ-substituted deconjugated butenolides to maleimides catalyzed by chiral squaramides†

Yun-Long Guo,ab   Li-Na Jia,ab   Lin Peng,a   Liang-Wen Qi,ab   Jing Zhou,ab   Fang Tian,a   Xiao-Ying Xu*a  and  Li-Xin Wang*a  

* Corresponding authors

a Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China
E-mail: wlxioc@cioc.ac.cn, xuxy@cioc.ac.cn
Fax: +86-028-8525-5208

b University of Chinese Academy of Sciences, Beijing 10039, People's Republic of China

Abstract

Highly enantioselective direct vinylogous Michael reactions of γ-aryl-substituted deconjugated butenolides with maleimides, catalyzed by only 1 mol% bifunctional squaramides derived from cinchona alkaloids, were achieved with excellent yields (up to 96%) and enantioselectivities (up to 97% ee). This protocol features a very low catalyst loading, mild reaction conditions and provides a potential and effective method for the construction of optically active chiral butenolides with adjacent quaternary and tertiary stereocenters.

Graphical abstract: Highly enantioselective direct vinylogous Michael addition of γ-substituted deconjugated butenolides to maleimides catalyzed by chiral squaramides

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Article information

DOI
https://doi.org/10.1039/C3RA43344G
Article type
Communication
Submitted
01 Jul 2013
Accepted
23 Jul 2013
First published
24 Jul 2013

RSC Adv., 2013,3, 16973-16976

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Highly enantioselective direct vinylogous Michael addition of γ-substituted deconjugated butenolides to maleimides catalyzed by chiral squaramides

Y. Guo, L. Jia, L. Peng, L. Qi, J. Zhou, F. Tian, X. Xu and L. Wang, RSC Adv., 2013, 3, 16973 DOI: 10.1039/C3RA43344G

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