Synfacts 2008(11): 1183-1183  
DOI: 10.1055/s-0028-1083428
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Ligand-Controlled Palladium-Catalyzed Asymmetric Allylic Alkylations

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

Publication History

Publication Date:
23 October 2008 (online)

Significance

Building on a previous report (B. M. Trost, J. Xu, M. Reichle J. Am. Chem. Soc. 2007, 129, 282), the authors describe the selective synthesis of a different regioisomer from the asymmetric allylic alkylation of 1,2-enediol carbonates. High yields and enantioselectivities are seen for the α-acyloxyketone products. Synthetic manipulations of the products via hydrogenation and olefin metathesis are also demonstrated.