153123-07-0

Upstream product

• 78-84-2 isobutyraldehyde 
• 153123-03-6 (E)-1-[(R)-p-tolylsulfinyl]-2-(trimethylsilyl)ethylene 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 
• 401614-03-7 1-phenylseleno-1-[(S)-p-tolylsulfinyl]-2-(trimethylsilyl)ethane 
• 153123-09-2 (R_S)-p-Tolyl β-(trimethylsilyl)ethyl sulfoxide 

Downstream Products

• 77943-78-3 (S)-4-methyl-1-pentyn-3-ol 

Relevant academic research and scientific papers

Preparation of optically pure propargylic and allylic alcohols from 2-(trimethylsilyl)vinyl sulfoxides as a chiral ethynyl anion synthon: Computational studies on elimination reaction of 2-(trimethylsilyl)vinyl sulfoxides

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.

Convenient Preparation of Optically Pure Propargylic Alcohols Using 2-(Trimethylsilyl)vinyl Sulfoxide As A Novel Chiral Synthon

Both enentiomers of optically pure propargylic alcohols are conveniently prepared by the reaction of α-vinyl anion of 2-(trimethylsilyl)vinyl p-tolyl sulfoxide with aldehydes and subsequent either desilylsulfination or thermal elimination of the sulfinyl group.