Asymmetric synthesis of isothiazoles through Cu catalysis: Direct catalytic asymmetric conjugate addition of allyl cyanide to α,β-unsaturated thioamides

Yuka Yanagida, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

Twice the catalyst: The simultaneous activation of an allyl cyanide (pronucleophile) and an α,β-unsaturated thioamide (electrophile) was achieved using a Cu-based soft Lewis acid/hard Brønsted base cooperative catalyst, thus resulting in the formation of enethioamides 1 in a highly enantio- and Z-selective manner (see scheme). The sequential Cu-catalyzed intramolecular cyclization gave rise to enantioenriched fused isothiazoles 2.

Original languageEnglish
Pages (from-to)7910-7914
Number of pages5
JournalAngewandte Chemie - International Edition
Volume50
Issue number34
DOIs
Publication statusPublished - 2011 Aug 16
Externally publishedYes

Keywords

  • allyl cyanides
  • asymmetric catalysis
  • cyclization
  • homogeneous catalysis
  • isothiazoles

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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