Circular dichroism spectral and chemical arguments for retention of configuration at sulfur in the Andersen synthesis of sterically hindered chiral sulfoxides

Abstract

Comparison of the circular dichroism (CD) spectra of isomeric butyl ethyl sulfoxides, prepared from (–)-(S)-O-n-propyl ethanesulfinate and (–)-(S)-O-n-propyl tert-butanesulfinate with the appropriate organomagnesium reagents, as well as experiments on the synthesis of (–)-(R)-n-butyl tert-butyl sulfoxide strongly suggest retention of configuration in the reactions of either nonbranched alkanesulfinates with hindered organometallic reagents or sulfinates containing sterically demanding substituents at the sulfinyl sulfur atom with nonhindered organometallics.