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Synfacts 2005(2): 0240-0240  
DOI: 10.1055/s-2005-916106
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of 3,3-Diarylpropanals with Chiral Diene-Rhodium Catalysts

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
J. F. Paquin, C. Defieber, C. R. J. Stephenson, E. M. Carreira*
ETH Hönggerberg, Zürich, Switzerland
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Publication History

Publication Date:
25 October 2005 (online)

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Significance

This paper describes a route to access 3,3-diarylpropanals in high enantioselectivity with two important results: (1) Highly enantio­enriched products are obtained where the aryl groups vary only slightly (i.e. differ only in para-substituent), and (2) both electron-rich and electron-poor aryl nucleophiles provide excellent results. The starting materials for these reactions are the readily available arylboronic acids and cinnamaldehydes.