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Organocatalytic Enantioselective α-Hydroxymethylation of Aldehydes: Mechanistic Aspects and Optimization

Robert K. Boeckman, Jr.*, Kyle F. Biegasiewicz, Douglas J. Tusch and John R. Miller

*Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, United States, Email:

R. K. Boeckman, Jr., K. F. Biegasiewicz, D. J. Tusch, J. R. Miller, J. Org. Chem., 2015, 80, 4030-4045.

DOI: 10.1021/acs.joc.5b00380

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A direct enantioselective α-hydroxymethylation of aldehydes employing an α,α-diarylprolinol trimethylsilyl ether organocatalyst enables efficient access to β-hydroxycarboxylic acids and δ-hydroxy-α,β-unsaturated esters via an intermediate lactol in good yields, excellent enantioselectivity, and compatibility with a broad range of functional groups in the aldehyde.

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Key Words

β-hydroxy carboxylic acids, oxidation, sodium chlorite, organocatalysis

ID: J42-Y2015