Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides

Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticle

113 Citations (Scopus)

Abstract

Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides under proton transfer conditions is described. Soft Lewis acid/hard Brønsted base cooperative catalysis is crucial for simultaneous activation of terminal alkynes and thioamides, affording the β-alkynylthioamides in a highly enantioselective manner. Control experiments suggested that the intermediate copper thioamide enolate can work as Brønsted base to drive the catalytic cycle via proton transfer. The divergent transformation of the thioamide functionality highlights the synthetic utility of the alkynylation products.

Original languageEnglish
Pages (from-to)10275-10277
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number30
DOIs
Publication statusPublished - Aug 4 2010
Externally publishedYes

Fingerprint

Thioamides
Proton transfer
Alkynes
Catalysis
Protons
Chemical activation
Copper
Lewis Acids
Acids
Experiments

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides. / Yazaki, Ryo; Kumagai, Naoya; Shibasaki, Masakatsu.

In: Journal of the American Chemical Society, Vol. 132, No. 30, 04.08.2010, p. 10275-10277.

Research output: Contribution to journalArticle

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