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Synfacts 2006(8): 0835-0835
DOI: 10.1055/s-2006-942002
DOI: 10.1055/s-2006-942002
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Diethylzinc-Mediated Catalytic Asymmetric Allylation of Benzaldehydes
G. P. Howell, A. J. Minnaard, B. L. Feringa
University of Groningen, The Netherlands
Further Information
Publication History
Publication Date:
21 July 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200608/lookinside/thumbnails/10.1055-s-2006-942002-1.jpg)
Significance
The asymmetric allylic alkylation is one of the most valuable tools of enantioselective synthesis. This work is one of the first reports on a highly practical variant of this process: ”Umpolung allylation”, which uses allylic acetates and organometallic reagents like dialkylzinc or trialkylboron as equivalents to allylmetallic species. The authors optimized the catalyst and conditions for the reaction of cyclohexenyl acetate with aryl aldehydes, affording products with high stereoselectivity via a cyclic six-membered transition state.