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

Barry M. Trost,* Jiayi Xu and Markus Reichle

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

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

DOI: 10.1021/ja067342a

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Abstract

In a new, efficient, catalytic asymmetric protocol for the synthesis of α-tertiary hydroxyaldehydes from readily available α-halo or α-hydroxy ketones or enol silyl ethers, the chiral ligand controls the regioselectivity as well as the enantioselectivity.

see article for more examples

see article for more reactions

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

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

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Key Words

Carbonyl Compounds, Homoallylic Alcohols, Tsuji-Trost Reaction

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ID: J48-Y2007-0070