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Synfacts 2010(5): 0616-0616  
DOI: 10.1055/s-0029-1219730
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Polymer-Supported Chiral Organocatalysts for Diels-Alder Reaction

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Chung Keun Jin
N. Haraguchi*, Y. Takemura, S. Itsuno
Toyohashi University of Technology, Japan
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

Polymer-supported chiral organocatalysts 3a-e were prepared by ion exchange ­reaction of a chiral imidazolidin-4-one hydrochloride 2 (also known as MacMillan catalyst) with polymer-supported sulfonic acids 1a-e. The catalytic asymmetric Diels-Alder reaction of 1,3-cyclopentadiene (4) and trans-cinnamaldehyde (5) was performed with 3e to afford the bicyclic aldehydes 6 and 7 (>99% conversion, 6/7 = 56:44; 6: 88% ee, 7: 91% ee).