Structure of alcohols obtained by reaction of aldehydes and ketones with ortho-lithiated oxazolines

Abstract

The reaction of aldehydes with ortho-lithiated oxazolines typically gives secondary alcohols. Exceptionally, a case is described of the formation of a primary alcohol by the opening of the oxazoline ring. The reaction of ketones with ortho-lithiated oxazolines, in contrast to reports in the literature, typically gives primary alcohols, by opening of the oxazoline ring, and not the reported tertiary alcohols. The proposed structures are substantiated by the preparation of derivatives and, particularly, by consideration of the ¹³C n.m.r. spectra.