The reaction of the alpha-carbanion derived from (trimethylsilyl)vinyl sulfoxides with aldehydes afforded a diastereomeric mixture of the products. Each diastereomer was subjected to specific elimination reactions to give optically pure propargylic, trimethylsilylated propargylic, and allylic alcohols. Acceleration of the sulfenic acid-elimination from the beta-silylvinyl sulfoxide was demonstrated by the ab initio calculation to be ascribed mainly to the beta-effect of the silyl group.

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An exclusive one step synthesis of dihydropyridin-2-imines 2 or 3, both of which are potent inhibitors of inducible nitric oxide (iNOS), from the common starting material 2-aminopyridine 1 was successfully carried out using the Birch reduction followed by the appropriate work-up procedure. The application of this reduction to other substituted 2-aminopyridines 4-8 and 2-hydroxypyridine 9 are reported. The reaction mechanism is also discussed.

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