Lanthanum Tricyanide-Catalyzed Acyl Silane-Ketone Benzoin Additions

James C. Tarr and Jeffrey S. Johnson*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, Email: jsjunc.edu

J. C. Tarr, J. S. Johnson, Org. Lett., 2009, 11, 3870-3873.

DOI: 10.1021/ol901314w

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Abstract

Lanthanum tricyanide efficiently catalyzes a benzoin-type coupling between acyl silanes and ketones. Good yields are obtained over a broad substrate scope encompassing aryl, alkyl, and sterically hindered ketones.

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proposed mechanism

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Catalytic Nucleophilic Glyoxylation of Aldehydes

K. M. Steward, J. S. Johnson, Org. Lett., 2010, 12, 2864-2867.

Kinetic Control in Direct α-Silyloxy Ketone Synthesis: A New Regiospecific Catalyzed Cross Silyl Benzoin Reaction

X. Linghu, J. S. Johnson, Angew. Chem. Int. Ed., 2003, 42, 2534-2536.

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Key Words

Benzoins, Benzoin Condensation, Brook Rearrangement

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ID: J54-Y2009-2620