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Asymmetric Pauson−Khand-type Reaction Mediated by Rh(I) Catalyst at Ambient Temperature

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Dong Eun Kim^†, In Su Kim^†, Virginie Ratovelomanana-Vidal*^‡, Jean-Pierre Genêt*^‡ and Nakcheol Jeong*^†

Department of Chemistry, Korea University, Seoul, 136-701, Korea, and Laboratoire de Synthèse Sélective Organique et Produits Naturels, Ecole Nationale Supérieure de Chimie de Paris, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France

J. Org. Chem., 2008, 73 (20), pp 7985–7989

DOI: 10.1021/jo801236c

Publication Date (Web): September 18, 2008

, †

Korea University.

, ‡

Ecole Nationale Supérieure de Chimie de Paris.

Section:

General Organic Chemistry

Abstract

An efficient asymmetric PKR mediated by Rh(I) catalyst at ambient temperature was developed. The reaction utilizing a Rh(I) catalyst bearing a (R)-3,5-diMeC₄H₄-BINAP ligand at 18−20 °C under a reduced partial pressure of CO (0.1 atm) provided PKR products in high chemical yield as well as high enantioselectivity.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Reverse the Diastereoselectivity of the Rh(I)-Catalyzed Pauson-Khand Cycloaddition
Mark Turlington and Lin Pu
Organic Letters2011 13 (16), 4332-4335
- Reverse the Diastereoselectivity of the Rh(I)-Catalyzed Pauson-Khand Cycloaddition
  Mark Turlington and Lin Pu
  Organic Letters2011 13 (16), 4332-4335
  It is discovered that the diastereoselectivity of the Rh(I)-catalyzed Pauson–Khand cycloaddition of chiral enynes can be reversed to generate the trans diastereomer as the major product in the absence of a chelate phosphine ligand when the substrate ...
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Utilization of Aldoses as a Carbonyl Source in Cyclocarbonylation of Enynes
Keiichi Ikeda, Tsumoru Morimoto, and Kiyomi Kakiuchi
The Journal of Organic Chemistry2010 75 (18), 6279-6282
- Utilization of Aldoses as a Carbonyl Source in Cyclocarbonylation of Enynes
  Keiichi Ikeda, Tsumoru Morimoto, and Kiyomi Kakiuchi
  The Journal of Organic Chemistry2010 75 (18), 6279-6282
  The reaction of enynes with acetyl-masked aldoses in the presence of a rhodium(I) catalyst resulted in cyclocarbonylation, thus avoiding the direct use of carbon monoxide, to afford bicyclic cyclopentenones. In rhodium catalysis, aldoses serve as a carbon ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links