Efficient Hydroxyl Inversion in Propionates via Cesium Carboxylates

Abstract

A versatile method for hydroxyl inversion, based on cesium carboxylates, was developed for polypropionate precursors and models. This procedure is compatible with a number of functional groups, including 3,4-epoxy alcohols, which tend to cyclize under basic conditions. This strategy allowed the preparation of a series of diastereomeric alcohols and new 3,4-epoxy alcohols, not available by standard iodocyclization techniques.

Keywords:

• Hydroxyl inversion
• Cesium carboxylates
• 3,4-Epoxy alcohols

Acknowledgments

This work was supported by grants from the National Institutes of Health RISE (1R25-GM-61151-01A1) and SCORE (2S06GM-08102-29) programs. Financial support for L. Castro was provided by the Department of Education-Patricia Harris Fellowship Program. Partial support for the NMR facility was provided by the NIH-RCMI program (RR03641).