Format

Send to

Choose Destination
Org Lett. 2011 Mar 4;13(5):952-5. doi: 10.1021/ol102998w. Epub 2011 Feb 3.

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

Author information

1
Institute of Microbial Chemistry, Tokyo, Japan.

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.

PMID:
21291204
DOI:
10.1021/ol102998w
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center