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

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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.

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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: