Substituent Effect on the Enantioface-Differentiating Reaction of (R)- with m- or p-Substituted Acetophenones

Article abstract of DOI:10.1246/bcsj.65.526

When lithiomethyl p-tolyl sulfoxide derived from (R)-(+)- was allowed to react with acetophenones which have a variety of m- or p-substituents, the corresponding diastereomeric mixture of β-hydroxy sulfoxides (R_SS_C and R_SR_C) was produced.The degree of enantioselectivity was affected by the nature of the substituent on benzene ring.The logarithms of R_SS_C/R_SR_C values thus obtained gave a good correlation with Hammett's ? values, affording a negative straight line.The results have been discussed in view of the stereochemical course of the reaction.