Use of α-Chlorinated N-(tert-Butanesulfinyl)imines in the Synthesis of Chiral Aziridines

Bram Denolf,† Sven Mangelinckx,† Karl W. Törnroos,‡ and Norbert De Kimpe*†
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium, and Department of Chemistry, University of Bergen, Allegaten 41, N-5007 Bergen, Norway
Org. Lett., 2006, 8 (14), pp 3129–3132
DOI: 10.1021/ol0611245
Publication Date (Web): June 14, 2006
Copyright © 2006 American Chemical Society
†

 Ghent University.

,
‡

 University of Bergen.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, norbert.dekimpe@UGent.be

Abstract

Abstract Image

Reaction of chiral α-chloro tert-butanesulfinyl aldimines with Grignard reagents efficiently afforded β-chloro N-sulfinamides in high diastereomeric excess. The latter compounds were cyclized toward the corresponding chiral aziridines in a high-yielding one-pot reaction or after separate treatment with base. The diastereoselectivity obtained in the newly synthesized β-chloro sulfinamides is explained via the coordinating ability of the α-chloro atom with magnesium resulting in the opposite stereochemical outcome as generally observed for nonfunctionalized N-sulfinyl imines.

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History

  • Published In Issue July 06, 2006
  • Received May 8, 2006

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