Issue 51, 2013
From the journal:

Chemical Communications

Highly diastereoselective and enantioselective direct Michael addition of phthalide derivatives to nitroolefins†

Jie Luo,a   Haifei Wang,b   Fangrui Zhong,a   Jacek Kwiatkowski,a   Li-Wen Xuc  and  Yixin Lu*ac  

* Corresponding authors

a Department of Chemistry and Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
E-mail: chmlyx@nus.edu.sg

b Hunan University of Technology, Hunan, P. R. China

c Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, P. R. China
E-mail: liwenxu@hznu.edu.cn

Abstract

The first asymmetric Michael addition of 3-substituted phthalides to nitroolefins promoted by amino acid-incorporating multifunctional catalysts has been developed. The reported method led to the synthesis of 3,3-disubstituted phthalide derivatives in high yields, and in a highly diastereoselective and enantioselective manner. Facile synthesis of a chiral bicyclic lactam has also been demonstrated.

Graphical abstract: Highly diastereoselective and enantioselective direct Michael addition of phthalide derivatives to nitroolefins

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Article information

DOI
https://doi.org/10.1039/C3CC42187B
Article type
Communication
Submitted
26 Mar 2013
Accepted
07 May 2013
First published
09 May 2013

Chem. Commun., 2013,49, 5775-5777

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Highly diastereoselective and enantioselective direct Michael addition of phthalide derivatives to nitroolefins

J. Luo, H. Wang, F. Zhong, J. Kwiatkowski, L. Xu and Y. Lu, Chem. Commun., 2013, 49, 5775 DOI: 10.1039/C3CC42187B

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