Issue 27, 2011
From the journal:

Chemical Communications

Nickel(ii)-catalyzed diastereoselective [3+2] cycloaddition of N-tosyl-aziridines and aldehydesvia selective carbon–carbon bond cleavage†

Xingxing Wu,a   Lei Lia  and  Junliang Zhang*ab  

* Corresponding authors

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China
E-mail: jlzhang@chem.ecnu.edu.cn

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China

Abstract

An efficient and mild Ni(ClO4)2-catalyzed [3+2] cycloaddition of N-tosylaziridines and aldehydesvia C–C bond cleavage was developed. The cycloaddition reaction proceeds with high diastereoselectivity and regioselectivity leading to highly substituted 1,3-oxazolidines. Notably, this novel reaction can be easily expanded to gram level scale and the thermal conditions cannot achieve the same transformation.

Graphical abstract: Nickel(ii)-catalyzed diastereoselective [3+2] cycloaddition of N-tosyl-aziridines and aldehydesvia selective carbon–carbon bond cleavage

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Article information

DOI
https://doi.org/10.1039/C1CC12189H
Article type
Communication
Submitted
16 Apr 2011
Accepted
11 May 2011
First published
08 Jun 2011

Chem. Commun., 2011,47, 7824-7826

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Nickel(II)-catalyzed diastereoselective [3+2] cycloaddition of N-tosyl-aziridines and aldehydesvia selective carbon–carbon bond cleavage

X. Wu, L. Li and J. Zhang, Chem. Commun., 2011, 47, 7824 DOI: 10.1039/C1CC12189H

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