Synthesis 2003(14): 2169-2172
DOI: 10.1055/s-2003-41044
PAPER
© Georg Thieme Verlag Stuttgart · New York

Rh(I)-Catalyzed Asymmetric Intramolecular Pauson-Khand Reaction in Aqueous Media

Won Hyuck Suh, Mira Choi, Sang Ick Lee, Young Keun Chung*
School of Chemistry and Center for Molecular Catalysis, Seoul National University, Seoul 151-747, Korea
Fax: +82(2)8890310; e-Mail: ykchung@plaza.snu.ac.kr;
Further Information

Publication History

Received 20 May 2003
Publication Date:
28 August 2003 (online)

Abstract

The first rhodium-BINAP complex-catalyzed enantioselective Pauson-Khand reaction in aqueous media, which is accelerated by surfactant, is reported. The chiral rhodium catalyst is easily prepared in situ from 1 equivalent of [Rh(cod)Cl]2 and 2 equivalents of BINAP under 1 atm of CO and a temperature of 60 °C or 90 °C. Ee’s up to 96% were achieved for the intramolecular Pauson-Khand reaction, but the yields are highly dependent upon the substrate itself.