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Synfacts 2005(1): 0128-0128  
DOI: 10.1055/s-2005-916019
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Asymmetric 1,6-Addition of Aryl Zinc Reagents to Dienones

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Hayashi*, S. Yamamoto, N. Tokunaga
Kyoto University, Japan
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Publication History

Publication Date:
21 September 2005 (online)

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Significance

Rhodium-catalyzed 1,4-additions to α,β-unsaturated carbonyl compounds have been shown as one of the most efficient and reliable asymmetric transformations. This represents the first catalytic asymmetric 1,6-addition to 2,4-dienones. Both cyclic and linear 2,4-dienones were utilized with the former giving the best results. Various aryl sources were tested (B, Ti, Zn) with PhZnCl giving superior results.