Intermediate as catalyst: Catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides

Takanori Ogawa, Shinsuke Mouri, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

Catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides is promoted by a mesitylcopper/(R)-DTBM- Segphos precatalyst, affording γ-nitrothioamides in moderate to high syn-selectivity and excellent enantioselectivity. The intermediate Cu-thioamide enolate functions as a soft Lewis acid/hard Brønsted base cooperative catalyst to drive the catalytic cycle efficiently under proton transfer conditions.

Original languageEnglish
Pages (from-to)110-113
Number of pages4
JournalOrganic Letters
Volume14
Issue number1
DOIs
Publication statusPublished - 2012 Jan 6
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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