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Paper | Special issue | Vol 54, No. 2, 2001, pp.735-746
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)52
■ Stereospecific Substitution of 1-(2- Pyridinyl)ethyl Methanesulfonate with S- and O-Nucleophiles

Jun'ichi Uenishi,* Masahiro Hamada, Tomoko Takagi, and Osamu Yonemitsu

*Kyoto Pharmaceutical University, Misasagi-Shichonocho, Yamashina, Kyoto 607-8414, Japan

Abstract

Nucleophilic substitution reactions of (S)- and (R)-1-(2-pyridinyl)ethyl methanesulfonate with S- and O-nucleophiles are described. The reaction of S-nucelophiles, such as aryl- and alkylthiols, and thioacetic acid, gave substituted sulfide and thioacetate with inversion of the configurations. For the reaction of O-nucleophiles, sodium phenoxides gave aryl ethers in good yields stereospecifically, but sodium alkoxide gave complex mixtures including racemic alkyl ether. Reactions with sodium carboxylate afforded the corresponding ester stereospecifically.