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Inverted Diastereoselectivity in Asymmetric Aziridine Synthesis viaAza-Darzens Reaction of (2S)-N-Bromoacyl Camphorsultam

McLaren, Andrew B. and Sweeney, Joseph B. (1999) Inverted Diastereoselectivity in Asymmetric Aziridine Synthesis viaAza-Darzens Reaction of (2S)-N-Bromoacyl Camphorsultam. Organic Letters, 1 (9). pp. 1339-1341. ISSN 1523-7060
Abstract

The aza-Darzens reaction of the chiral enolate derived from (2S)-bromoacetyl camphor sultam (1) with certain C-3-substituted N-diphenylphosphinyl imines gives mixtures of trans- and cis-aziridines. In some cases, only trans isomers are observed. A steric repulsion between the enolate halogen atom and this C-3-substituent is invoked to rationalize these observations.

Information
URI:
https://eprints.hud.ac.uk/id/eprint/15295
URI:
https://eprints.hud.ac.uk/id/eprint/15295
Title:
Inverted Diastereoselectivity in Asymmetric Aziridine Synthesis viaAza-Darzens Reaction of (2S)-N-Bromoacyl Camphorsultam
Creators:
McLaren, Andrew B. and Sweeney, Joseph B.
Identification Number:
10.1021/ol990874u
Official URL:
http://dx.doi.org/10.1021/ol990874u
Date:
October 1999
Subjects:
Q Science > QD Chemistry
Schools:
School of Applied Sciences
Library
Item Type:
Article
Depositing User:
Joseph Sweeney
Date Deposited:
18 Oct 2012 10:21
Revision:
10
Last Modified:
28 Aug 2021 11:22
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