Propylene Glycol Cyclic Sulfate as a Substitute for Propylene Oxide in Reactions with Acetylides

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.

Acknowledgments

Generous financial support from the Thailand Research Fund is gratefully acknowledged. Preliminary experiments were supported by the Robert A. Welch Foundation.