Issue 9, 2015
From the journal:

Chemical Communications

Asymmetric synthesis of α-(1-oxoisoindolin-3-yl)glycine: synthetic and mechanistic challenges†

Tingting Li,ab   Shengbin Zhou,b   Jiang Wang,b   José Luis Aceña,c   Vadim A. Soloshonok*cd  and  Hong Liu*ab  

* Corresponding authors

a School of Pharmacy, China Pharmaceutical University, Jiangsu, Nanjing 210009, China

b Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, China
E-mail: hliu@simm.ac.cn

c Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain

d IKERBASQUE, Basque Foundation for Science, María Díaz de Haro 3, 48013 Bilbao, Spain

Abstract

We report herein that the NaOMe-catalyzed reactions between the chiral glycine Schiff base (S)-4 with 2-cyanobenzaldehyde 3a provide for a convenient preparation of the novel α-(1-oxoisoindolin-3-yl)glycine 1 of high pharmaceutical potential. The reactions involve at least eight synthetic steps and can mechanistically be realized only with application of Ni(II) complexes described in this study.

Graphical abstract: Asymmetric synthesis of α-(1-oxoisoindolin-3-yl)glycine: synthetic and mechanistic challenges

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Article information

DOI
https://doi.org/10.1039/C4CC05659K
Article type
Communication
Submitted
24 Jul 2014
Accepted
02 Dec 2014
First published
02 Dec 2014

Chem. Commun., 2015,51, 1624-1626

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Asymmetric synthesis of α-(1-oxoisoindolin-3-yl)glycine: synthetic and mechanistic challenges

T. Li, S. Zhou, J. Wang, J. L. Aceña, V. A. Soloshonok and H. Liu, Chem. Commun., 2015, 51, 1624 DOI: 10.1039/C4CC05659K

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