Issue 13, 2011
From the journal:

Chemical Communications

Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines†

Yan Zhang,a   Choon Wee Kee,a   Richmond Lee,b   Xiao Fu,a   Julian Ying-Teck Soh,a   Esther Mun Foong Loh,a   Kuo-Wei Huang*b  and  Choon-Hong Tan*a  

* Corresponding authors

a Department of Chemistry, 3 Science Drive 3, National University of Singapore (NUS), 117543 Singapore, Singapore
E-mail: chmtanch@nus.edu.sg
Fax: +65 6779 1691
Tel: +65 6516 2845

b KAUST catalysis Center and Division of Chemicals and Life Sciences and Engineering, King Abdullah University of Science and Technology, Thuwal 23955-6900, Kingdom of Saudi Arabia
E-mail: hkw@kaust.edu.sa

Abstract

An amino-indanol derived chiral guanidine was developed as an efficient Brønsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products in high yields and enantioselectivities.

Graphical abstract: Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines

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Article information

DOI
https://doi.org/10.1039/C0CC05840H
Article type
Communication
Submitted
30 Dec 2010
Accepted
02 Feb 2011
First published
21 Feb 2011

Chem. Commun., 2011,47, 3897-3899

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Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines

Y. Zhang, C. W. Kee, R. Lee, X. Fu, J. Y. Soh, E. M. F. Loh, K. Huang and C. Tan, Chem. Commun., 2011, 47, 3897 DOI: 10.1039/C0CC05840H

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