Direct conversion of activated alcohols to azides using diphenyl phosphorazidate. A practical alternative to Mitsunobu conditions

…, GR Humphrey, AM DeMarco, DJ Mathre…

Index: Thompson, Andrew S.; Humphrey, Guy R.; DeMarco, Anthony M.; Mathre, David J.; Grabowski, Edward J. J. Journal of Organic Chemistry, 1993 , vol. 58, # 22 p. 5886 - 5888

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Citation Number: 264

Abstract

Summary: Fourteen alcohols were converted to their corresponding azides with inversion of configuration using diphenyl phosphorazidate and DBU. ... While evaluating a new route to a potential elastase inhibitor,l we required the conversion of optically active alcohol 1 into azide 2. Since the starting alcohol was enantiomerically pure? introduction of the azide would have to proceed with clean 8N2 inversion. Our initial efforts using a sulfonate derivative were ...