Efficient Preparation of γ-Hydroxynitriles via Nitrile Enolate-Epoxide Reactions: Scope and Diastereoselectivity

Abstract

The nucleophilic opening of epoxides by nitrile enolates using an efficient, convenient protocol is described. The diastereoselectivity of this reaction was explored and found to give syn:anti ratios ranging from 1.1:1.0 to 4.8:1.0.

‡ Camille and Henry Dreyfus Scholar/Fellow 1995–1997.

Notes

‡ Camille and Henry Dreyfus Scholar/Fellow 1995–1997.

This was determined by converting 5c to the corresponding lactone via microbial nitrile hydrolysis³ (known not to epimerize α-stereocenters) and comparing the ¹H NMR resonances for the major isomer to literature data of known cis and trans 2,4-disubstituted lactones.