Ligand Controlled Highly Regio- and Enantioselective Synthesis of α-Acyloxyketones by Palladium-Catalyzed Allylic Alkylation of 1,2-Enediol Carbonates

Barry M. Trost*, Jiayi Xu and Thomas Schmidt

*Department of Chemistry, Stanford University, Stanford, California 94305-5080, Email: bmtroststanford.edu

B. M. Trost, J. Xu, T. Schmidt, J. Am. Chem. Soc., 2008, 130, 11852-11853.

DOI: 10.1021/ja8038954

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Abstract

The palladium catalyzed decarboxylative asymmetric allylic alkylation of allyl 1,2-enediol carbonates gives exclusively α-hydroxyketones in very good yields and high enantiomeric excesses using L_naph as ligand in DME. The reaction proceeds under extremely mild conditions and tolerates a broad range of esters.

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Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates

B. M. Trost, J. Xu, M. Reichle, J. Am. Chem. Soc., 2007, 129, 282-283.

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Key Words

Homoallylic Alcohols, Carbonyl Compounds, Tsuji-Trost Reaction

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ID: J48-Y2008-2360