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Synfacts 2009(3): 0349-0349  
DOI: 10.1055/s-0028-1087732
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Supported Vanadium Catalysts for Kinetic Resolution

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada
R. A. Shiels, K. Venkatasubbaiah, C. W. Jones*
Georgia Institute of Technology, Atlanta, USA
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

Oxidative kinetic resolution of α-hydroxy esters with a polymer-supported vanadium catalyst 1 is reported. Thus, radical polymerization of a Schiff base 2 and divinylbenzene followed by complexation with VO(Oi-Pr)3 gave a polystyrene resin supported vanadyl complex 1. The oxidative kinetic resolution of α-hydroxy esters 3 was performed with 5.5 mol% of 1 in acetone under O2 atmosphere for 9-87 h to give the optically active substrates 3 with 77-95% ee in 52-63% conversion (s = 12-23). The catalyst was reused three times without loss of catalytic activity.