Chiral Brønsted Acid Catalyzed Enantioconvergent Propargylic Substitution Reaction of Racemic Secondary Propargylic Alcohols with Thiols

Jun Kikuchi, Kyohei Takano, Yusuke Ota, Shigenobu Umemiya, Masahiro Terada

研究成果: Article査読

4 被引用数 (Scopus)

抄録

Despite the significant progress of the enantioselective reaction using chiral catalysts, the enantioselective nucleophilic substitution reaction at the chiral sp3-hybridized carbon atom of a racemic electrophile has not been largely explored. Herein, we report the enantioconvergent propargylic substitution reaction of racemic propargylic alcohols with thiols using chiral bis-phosphoric acid as the chiral Brønsted acid catalyst. The substitution products were formed in high yields with high enantioselectivities in most cases. The cation-stabilizing effect of the sulfur functional group introduced at the alkynyl terminus is the key to achieving the efficient enantioconvergent process, in which chiral information originating from not only the racemic stereogenic center but also the formed contact ion pair is completely eliminated from the present system.

本文言語English
ページ(範囲)11124-11128
ページ数5
ジャーナルChemistry - A European Journal
26
49
DOI
出版ステータスPublished - 2020 9 1

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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