Issue 42, 2012
From the journal:

Chemical Communications

Organocatalytic stereocontrolled synthesis of 3,3′-pyrrolidinyl spirooxindoles by [3+2] annulation of isocyanoesters with methyleneindolinones†

Liang-Liang Wang,ab   Jian-Fei Bai,ab   Lin Peng,a   Liang-Wen Qi,ab   Li-Na Jia,ab   Yun-Long Guo,ab   Xi-Ya Luo,ab   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, China
E-mail: wlxioc@cioc.ac.cn, xuxy@cioc.ac.cn

b Graduate School of Chinese Academy of Sciences, Beijing, China

Abstract

A stereoselective [3+2] cycloaddition of isocyanoesters to methyleneindolinones catalyzed by a quinine-based thiourea-tertiary amine has been successfully developed. Just by tuning the protecting groups on substrates, a variety of optically enriched 3,3′-pyrrolidinyl spirooxindole diastereomers could be obtained in excellent enantioselectivities (up to 99% ee).

Graphical abstract: Organocatalytic stereocontrolled synthesis of 3,3′-pyrrolidinyl spirooxindoles by [3+2] annulation of isocyanoesters with methyleneindolinones

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Article information

DOI
https://doi.org/10.1039/C2CC30746D
Article type
Communication
Submitted
02 Feb 2012
Accepted
30 Mar 2012
First published
02 Apr 2012

Chem. Commun., 2012,48, 5175-5177

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Organocatalytic stereocontrolled synthesis of 3,3′-pyrrolidinyl spirooxindoles by [3+2] annulation of isocyanoesters with methyleneindolinones

L. Wang, J. Bai, L. Peng, L. Qi, L. Jia, Y. Guo, X. Luo, X. Xu and L. Wang, Chem. Commun., 2012, 48, 5175 DOI: 10.1039/C2CC30746D

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