Synfacts 2005(1): 0180-0180  
DOI: 10.1055/s-2005-916003
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Diels-Alder Reaction Using a Polymer-Supported N-P Type Ligand

Contributor(s): Yasuhiro Uozumi, Maki Minakawa
H. Nakano*, K. Takahashi, R. Fujita
Tohoku Pharmaceutical University, Japan
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21. September 2005 (online)


A cationic palladium complex of a polystyrene-ethyl (PS-Et)-supported chiral phosphinooxazoline ligand provided excellent enantio­selectivity (92% ee) in the asymmetric Diels-Alder reaction of cyclopentadiene (2) with acryloyl-1,3-oxazolidine-2-one (3). The polymeric catalyst 1 was recycled with approximately 30% loss in both activity (from 79% to 45% yield) and enantioselectivity (from 92% to 62% ee).