Inverted diastereoselectivity in asymmetric aziridine synthesis via aza-Darzens reaction of (2S)-N-bromoacyl camphorsultam

Authors
McLaren, AB Sweeney, JB
Citation
Ab. Mclaren et Jb. Sweeney, Inverted diastereoselectivity in asymmetric aziridine synthesis via aza-Darzens reaction of (2S)-N-bromoacyl camphorsultam, ORG LETT, 1(9), 1999, pp. 1339-1341
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
9
Year of publication
1999
Pages
1339 - 1341
Database
ISI
SICI code
1523-7060(19991104)1:9<1339:IDIAAS>2.0.ZU;2-W
Abstract
[GRAGHICS] The aza-Darzens reaction of the chiral enolate derived from (2S) bromoacety l camphor sultam (1) with certain C-3-substituted N-diphenylphosphinyl imin es gives mixtures of trans- and cis-aziridines. In some cases, only trans i somers are observed. A steric repulsion between the enolate halogen atom an d this C-3-substituent is invoked to rationalize these observations.