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

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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