Direct Catalytic Asymmetric Conjugate Addition of Saturated and Unsaturated Thioamides

Nilanjana Majumdar, Akira Saito, Liang Yin, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Direct catalytic asymmetric conjugate addition of thiolactams to α,β-unsaturated thioamides was efficiently promoted by a soft Lewis acid/hard Brønsted base cooperative catalyst in a highly stereocontrolled manner. Thioamide functionality was crucial to promote both the efficient enolization of thiolactam pronucleophiles and the subsequent stereoselective conjugate addition to α,β-unsaturated thioamides. Differential manipulation of the two thioamide functionalities of the product highlights the synthetic utility of the present catalytic system. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)3362-3365
Number of pages4
JournalOrganic Letters
Volume17
Issue number13
DOIs
Publication statusPublished - 2015 Jul 2
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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