Synfacts 2007(4): 0390-0390  
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

Contributor(s): Mark Lautens, Praew Thansandote
B. M. Trost*, J. Xu, M. Reichle
Stanford University, USA
Further Information

Publication History

Publication Date:
23 March 2007 (online)

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.