Issue 14, 2010
From the journal:

Organic & Biomolecular Chemistry

Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across α-chloro N-sulfinylketimines†‡

Filip Colpaert,a   Sven Mangelinckx,§a   Erika Leemans,a   Bram Denolfa  and  Norbert De Kimpe*a  

* Corresponding authors

a Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
E-mail: norbert.dekimpe@UGent.be
Fax: +32 (0)9 264 62 43
Tel: +32 (0)9 264 59 51

Abstract

Reaction of chiral α-chloro N-tert-butanesulfinyl ketimines with Grignard reagents afforded new chiral N-sulfinyl 2,2-disubstituted aziridines in good to excellent diastereomeric ratio (dr up to 98 : 2). The 1,2,2-trisubstituted aziridines were isolated in high overall yield (51–85%) and with excellent enantiomeric excess (>98% ee). The stereoselectivity obtained in the Grignard addition is rationalized by the coordinating ability of the α-chloro atom resulting in the opposite stereochemical outcome as observed for nonfunctionalized N-sulfinyl ketimines.

Graphical abstract: Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across α-chloro N-sulfinyl ketimines

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Article information

DOI
https://doi.org/10.1039/C001471K
Article type
Paper
Submitted
22 Jan 2010
Accepted
04 May 2010
First published
25 May 2010

Org. Biomol. Chem., 2010,8, 3251-3258

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Asymmetric synthesis of new chiral N-sulfinyl 2,2-disubstituted aziridines by Grignard additions across α-chloro N-sulfinyl ketimines

F. Colpaert, S. Mangelinckx, E. Leemans, B. Denolf and N. De Kimpe, Org. Biomol. Chem., 2010, 8, 3251 DOI: 10.1039/C001471K

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