Stereospecific Substitution of 1-(2-Pyridinyl)ethyl Methanesulfonate with S- and O-Nucleophiles

Nucleophilic substitution reactions of ( 9 -and (R)-1-(2-pyridiny1)ethyl methanesulfonate with S-and 0-nucleophiles are described.The reaction of Snucelophiles, such as aryl-and alkylthlols, and thioacetic acid, gave substituted sulfide and thioacetate with inversion of the configurations.For the reaction of Onucleophiles, 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.