Enantioselective synthesis of a GPR40 agonist AMG 837 via catalytic asymmetric conjugate addition of terminal alkyne to α,β-unsaturated thioamide

Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

A concise enantioselective synthetic route to a potent GPR40 agonist AMG 837 is described. The crucial catalytic asymmetric conjugate addition of terminal alkyne was promoted by a soft Lewis acid/hard Brønsted base cooperative catalyst, allowing efficient construction of the requisite stereogenic center. The thioamide functional group is key to both activation in asymmetric alkynylation and facile transformation into carboxylic acid.(Figure Presented)

Original languageEnglish
Pages (from-to)952-955
Number of pages4
JournalOrganic Letters
Volume13
Issue number5
DOIs
Publication statusPublished - Mar 4 2011
Externally publishedYes

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Thioamides
Lewis Acids
Alkynes
alkynes
Carboxylic Acids
carboxylic acids
Functional groups
Chemical activation
routes
activation
catalysts
acids
Catalysts
synthesis
AMG 837

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Enantioselective synthesis of a GPR40 agonist AMG 837 via catalytic asymmetric conjugate addition of terminal alkyne to α,β-unsaturated thioamide. / Yazaki, Ryo; Kumagai, Naoya; Shibasaki, Masakatsu.

In: Organic Letters, Vol. 13, No. 5, 04.03.2011, p. 952-955.

Research output: Contribution to journalArticle

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