Tetrahedron

Electrophilic amination of enolates with oxaziridines: effects of oxaziridine structure and reaction conditions

A Armstrong, ID Edmonds, ME Swarbrick…

Index: Armstrong, Alan; Edmonds, Ian D.; Swarbrick, Martin E.; Treweeke, Nigel R. Tetrahedron, 2005 , vol. 61, # 35 p. 8423 - 8442

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Citation Number: 26

Abstract

A range of N-alkoxycarbonyl-and N-carboxamido-oxaziridines has been prepared to test the effects of oxaziridine structure on yields of enolate amination product. Side-products arising from reaction of aldehyde-derived oxaziridines with base were identified, while a ketone- derived oxaziridine afforded moderate yields of amination product with stabilised carbanions.