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

N Kunieda, J Nokami, M Kinoshita

Index: Kunieda, Norio; Nokami, Junzo; Kinoshita, Masayoshi Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 2 p. 526 - 529

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Citation Number: 4

Abstract

When lithiomethyl p-tolyl sulfoxide derived from (R)-(+)-[methyl p-tolyl sulfoxide] was allowed to react with acetophenones which have a variety of m-or p-substituents, the corresponding diastereometic mixture of β-hydroxy sulfoxides (R s S c and R s R c) was produced. The degree of enantioselectivity was affected by the nature of the substituent on benzene ring. The logarithms of the R s S c/R s R c values thus obtained gave a good correlation with ...