Diazo??Transfer Reaction with Diphenyl Phosphorazidate

…, A Enderli, A Linden, H Heimgartner

Index: Villalgordo, Jose M.; Enderli, Adelheid; Linden, Anthony; Heimgartner, Heinz Helvetica Chimica Acta, 1995 , vol. 78, # 8 p. 1983 - 1998

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Citation Number: 22

Abstract

Abstract Diphenyl phosphorazidate (DPPA) was used as the azide source in a one-pot synthesis of 2, 2-disubstituted 3-amino-2H-azirines 1 (Scheme 1). The reaction with lithium enolates of amides of type 2, bearing two substituents at C (2), proceeded smoothly in THF at 0; keteniminium azides C and azidoenamines D are likely intermediates. Under analogous reaction conditions, DPPA and amides of type 3 with only one substituent at C ( ...