Format

Send to

Choose Destination
Org Lett. 2014 Oct 3;16(19):5172-5. doi: 10.1021/ol502526y. Epub 2014 Sep 23.

O-Monoacyltartaric acid catalyzed enantioselective conjugate addition of a boronic acid to dienones: application to the synthesis of optically active cyclopentenones.

Author information

1
Graduate School of Pharmaceutical Sciences, Kumamoto University , 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan.

Abstract

Enantioselective conjugate addition of styrylboronic acid to dienones was effectively catalyzed by an O-monoacyltartaric acid to afford monostyrylated products with good enantioselectivity. The RCM of the monostyrylated products using the Hoveyda-Grubbs II catalyst afforded optically active cyclopentenones, including a synthetic intermediate of the antitumor agent TEI-9826. The study shows that a diene additive such as 1,6-heptadiene or diallyl ether was essential for the RCM.

PMID:
25248134
DOI:
10.1021/ol502526y
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center