Asymmetric Michael Reaction of α-CF3 Thioester and α,β-Unsaturated Aldehyde Catalyzed by Diphenylprolinol Silyl Ether

Yujiro Hayashi, Tomoaki Yamada, Misaki Sato, Shoya Watanabe, Eunsang Kwon, Kotaro Iwasaki, Shigenobu Umemiya

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Asymmetric Michael reaction of α-CF3 thioester and α,β-unsaturated aldehyde is catalyzed by diphenylprolinol silyl ether to afford the trifluoromethyl substituted Michael product with excellent enantioselectivity. Although the Michael products were generated as a mixture of syn- and anti-isomers, they can be transformed to single isomers of other useful compounds, such as lactone, lactam, piperidine, dihydropyran containing trifluoromethyl groups, or fluoro substituents.

Original languageEnglish
Pages (from-to)5183-5186
Number of pages4
JournalOrganic letters
Volume21
Issue number13
DOIs
Publication statusPublished - 2019 Jun 18

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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