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Diastereoselective Cobalt-Catalyzed Aldol and Michael Cycloreductions

Tae-Gon Baik, Ana Liza Luis, Long-Cheng Wang and Michael J. Krische*

*Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, Email:

T.-G. Baik, A. L. Luis, L.-C. Wang, M. J. Krische, J. Am. Chem. Soc., 2001, 123, 5112-5113.

DOI: 10.1021/ja0040971

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Catalytic enone hydrometallation represents a promising strategy for enolate generation, circumventing the utilization of preformed enol or enolate derivatives. Metal-catalyzed reductive condensation of α,β-unsaturated carbonyl compounds with aldehydes in the presence of a hydride donor enables highly diastereoselective aldol and Michael cycloreductions.

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proposed mechanism

Borane-Mediated Aldol Cycloreduction of Monoenone Monoketones: Diastereoselective Formation of Quaternary Centers

R. R. Huddleston, D. F. Cauble, M. J. Krische, J. Org. Chem., 2003, 68, 11-14.

Key Words

β-hydroxy ketones, cyclohexanols, phenylsilane

ID: J48-Y2001