Propylene glycol cyclic sulfate as a substitute for propylene oxide in reactions with acetylides

RW Bates, TB Maiti

Index: Bates, Roderick W.; Maiti, Tushar B. Synthetic Communications, 2003 , vol. 33, # 4 p. 633 - 640

Full Text: HTML

Citation Number: 5

Abstract

Abstract Lithium acetylides react cleanly with propylene glycol cyclic sulfate to give, after acidic hydrolysis, homopropargylic alcohols in good yield. The benzyl and TBDPS protecting groups are stable to these conditions, but the THP, TBS, acetal and orthoester groups are not. The readily available (S)-cyclic sulfate gives the (S)-alcohol without loss of stereochemical integrity.