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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Asymmetric Rhodium-catalyzed Intramolecular Hydroacylation for Fivemembered Ring Ketone Formation

Author(s): Masakazu Tanaka, Kiyoshi Sakai and Hiroshi Suemune

Volume 7, Issue 4, 2003

Page: [353 - 367] Pages: 15

DOI: 10.2174/1385272033372860

Price: $65

Abstract

The rhodium-catalyzed intramolecular hydroacylation of unsaturated aldehydes leads to the formation of cyclopentanone derivatives. The cyclization catalyzed by Wilkinsons complex is highly diastereoselective, and via this reaction, 3,4-disubstituted 4-pentenals were used to prepare the four stereoisomers of 3,4-disubstituted cyclopentanones. Several biologically active molecules, including 8- isoprostanoic acid, prostanoic acid, (-)-brefeldin A, 11-deoxyprostaglandin, and the nepetalactones,, have been synthesized in enantiomerically pure form from these cyclopentanones. In this review, the asymmetric synthesis of cyclopentanones via the enantioselective cyclization catalyzed by rhodium complex incorporating optically active ligands will be discussed.

Keywords: rhodium-catalyzed intramolecular hydroacylation, ring ketone formation, cyclopentanone derivative, optically active ligands


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