Electrophilic amination: preparation and use of N-Boc-3-(4-cyanophenyl) oxaziridine, a new reagent that transfers a N-Boc group to N-and C-nucleophiles

J Vidal, L Guy, S Sterin, A Collet

Index: Vidal, Joelle; Guy, Laure; Sterin, Sebastien; Collet, Andre Journal of Organic Chemistry, 1993 , vol. 58, # 18 p. 4791 - 4793

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Citation Number: 98

Abstract

Summary: We describe the preparation of the title compound 2b via aza-Wittig reaction of N- Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b. Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give Ng-Boc- hydrazines) and enolates (to give N-Boc-amino derivatives).

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