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Synfacts 2007(4): 0390-0390
DOI: 10.1055/s-2007-968339
DOI: 10.1055/s-2007-968339
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates
B. M. Trost*, J. Xu, M. Reichle
Stanford University, USA
Further Information
Publication History
Publication Date:
23 March 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200704/lookinside/thumbnails/10.1055-s-2007-968339-1.jpg)
Significance
The first example of a palladium-catalyzed highly enantioselective synthesis of α-tertiary hydroxyaldehydes is described using allylic alkylation of siloxy enol carbonates. The reaction proceeds under mild conditions and the substrates can be readily made from α-halo or α-hydroxy ketones. The scope is also broad, encompassing various protecting groups and substituents on the enol ether with excellent yields and enantioselectivities. The synthetic utility of the methodology is demonstrated by converting one product into a key precursor for the synthesis of the anticholinergic drug (S)-oxybutynin.