Journal of Organic Chemistry p. 640 - 647 (2002)
Update date:2022-08-05
Topics: DFT calculations Stereochemical Control Isolation and Characterization Elimination Reaction Transition State Analysis Solvent Effects
Nakamura, Shuichi
Kusuda, Shinya
Kawamura, Kiyoshi
Toru, Takeshi
The reaction of the (α-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 β-silylvinyl sulfoxide was demonstrated by the ab initio calculation to be ascribed mainly to the β-effect of the silyl group.
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