Issue 21, 2007
From the journal:

Organic & Biomolecular Chemistry

Rh-catalyzed highly enantioselective formation of functionalized cyclopentanes and cyclopentanones†

Fei Liu,a   Qiang Liu,a   Minsheng He,b   Xumu Zhang*ab  and  Aiwen Lei*ab  

* Corresponding authors

a College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, P. R. China
E-mail: aiwenlei@whu.edu.cn
Fax: +86 27 6875 4067
Tel: +86 27 6875 4672

b Department of Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania, USA

Abstract

A catalyst system, [Rh(COD)Cl]2–BINAP–AgSbF6, has been developed as a second-generation catalyst for the cycloisomerization of 1,6-enynes tethered by carbon chains. Cyclopentanes and cyclopentanones, which can contain functional groups, such as the 1,4-dienes, vinyl ether, aldehyde etc., were obtained from readily available starting materials in high yields and selectivities. Both regioselectivities and enantioselectivities are excellent: only 1,4-dienes were observed and in over 99% ee.

Graphical abstract: Rh-catalyzed highly enantioselective formation of functionalized cyclopentanes and cyclopentanones

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Article information

DOI
https://doi.org/10.1039/B712396E
Article type
Paper
Submitted
13 Aug 2007
Accepted
17 Sep 2007
First published
27 Sep 2007

Org. Biomol. Chem., 2007,5, 3531-3534

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Rh-catalyzed highly enantioselective formation of functionalized cyclopentanes and cyclopentanones

F. Liu, Q. Liu, M. He, X. Zhang and A. Lei, Org. Biomol. Chem., 2007, 5, 3531 DOI: 10.1039/B712396E

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