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

Xin Linghu, Jeffrey S. Johnson*

*Department of Chemistry, University of North Carolina, Chapel Hill, Chapel Hill, NC 27599-3290, USA, Email:

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

DOI: 10.1002/anie.200250554


Operationally simple cyanide-catalyzed silyl benzoin reactions afforded unsymmetrical aryl-, heteroaryl-, and alkyl-substituted silyl ether protected benzoin adducts with complete regiocontrol.

see article for more examples

proposed mechanism

Lanthanum Tricyanide-Catalyzed Acyl Silane-Ketone Benzoin Additions

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

Mechanism and Scope of the Cyanide-Catalyzed Cross Silyl Benzoin Reaction

X. Linghu, C. C. Bausch, J. S. Johnson, J. Am. Chem. Soc., 2005, 127, 1833-1840. DOI: 10.1021/ja044086y

Key Words

Benzoin Condensation, Brook Rearrangement, α-hydroxy carbonyls, ketones, phase-transfer catalysis, rearrangements, umpolung

ID: J06-Y2003-120