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Asymmetric aziridine synthesis by aza-Darzens reaction of N-diphenylphosphinylimines with chiral enolates. Part 1: formation of cis-aziridines

Sweeney, J.B., Cantrill, A.A., McLaren, A.B. and Thobhani, S. (2006) Asymmetric aziridine synthesis by aza-Darzens reaction of N-diphenylphosphinylimines with chiral enolates. Part 1: formation of cis-aziridines. Tetrahedron, 62 (15). pp. 3681-3693. ISSN 0040-4020

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To link to this article DOI: 10.1016/j.tet.2006.01.068

Abstract/Summary

Theaza-Darzens ('ADZ') reactions off-diphenylphosphinyl (W-Dpp') imines with chiral enolates derived from oxazolidinones and camphorsultam have been Studied. Whilst oxazolidinone enolates reacted poorly in terms of aziridination, the use of the chiral enolate derived from both antipodes of N-bromoacetyl 2, 10-camphorsultam, 2R-(5) and 2S-(5), with N-diphehenylphosphinyl aryl and tert-butylimines proceeded in generally good yield to give, respectively, (2'R,3'R)- or (2'S,3'S)-cis-N-diphenylphosphinyl aziridinoyl sultams of high de. (c) 2006 Elsevier Ltd. All rights reserved.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11646
Uncontrolled Keywords:aza-Darzens, aziridination, imine, camphorsultam, RING-OPENING REACTIONS, VINYL AZIRIDINES, COMPLEX, CONDENSATION, AMINATION, ALDEHYDES, EPOXIDES, REAGENTS, OLEFINS, FACILE

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