Metal-Catalyzed Reductive Aldol Coupling

Modern Reduction Methods

Volumn , Issue , 2008, Pages 387-417

  Garner, Susan A ^a   Han, Soo Bong ^b   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b NONE

Author keywords

Enolate generation from enones; Metal catalyzed reductive aldol coupling; Miscellaneous reductions; Reduction methods; Reductive aldol reaction

Indexed keywords

EID: 84891010485     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527622115.ch16     Document Type: Chapter

References (153)

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102. Chiu, P. (2004) Organosilanes in Copper-Mediated Conjugate Reductions and Reductive Aldol Reactions. Synthesis, 2210.
103. Nishiyama, H. and Shiomi, T. (2007) Reductive Aldol, Michael and Mannich Reactions. Topics in Current Chemistry, 279, 105.
104. For rhodium-catalyzed reductive aldol reaction mediated by hydrogen, see: Jang, H.Y., Huddleston, R.R. and Krische, M.J. (2002) Reductive Generation of Enolates from Enones Using Elemental Hydrogen: Catalytic C-C Bond Formation under Hydrogenative Conditions. Journal of the American Chemical Society, 124, 15156.
105. Huddleston, R.R. and Krische, M.J. (2003) Enolate Generation under Hydrogenation Conditions: Catalytic Aldol Cycloreduction of Keto-Enones. Organic Letters, 5, 1143.
106. Koech, P.K. and Krische, M.J. (2004) Catalytic Addition of Metallo-Aldehyde Enolates to Ketones: A New C-C Bond-Forming Hydrogenation. Organic Letters, 6, 691.
107. Marriner, G.A., Garner, S.A., Jang, H.Y. and Krische, M.J. (2004) Metallo-Aldehyde Enolates via Enal Hydrogenation: Catalytic Cross Aldolization with Glyoxal Partners As Applied to the Synthesis of 3, 5-Disubstituted Pyridazines. Journal of Organic Chemistry, 69, 1380.
108. Jung, C.K., Garner, S.A. and Krische, M.J. (2006) Hydrogen-Mediated Aldol Reductive Coupling of Vinyl Ketones Catalyzed by Rhodium: High Syn-Selectivity through the Effect of Tri-2-Furylphosphine. Organic Letters, 8, 519.
109. Han, S.B. and Krische, M.J. (2006) Reductive Aldol Coupling of Divinyl Ketones via Rhodium-Catalyzed Hydrogenation: syn-Diastereoselective Construction of β-Hydroxyenones. Organic Letters, 8, 5657.
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111. For cobalt-catalyzed reductive aldol reaction, see: Isayama, S. and Mukaiyama, T. (1989) Cobalt(II) Catalyzed Coupling Reaction of a, β-Unsaturated Compounds with Aldehydes by the Use of Phenylsilane. New Method for Preparation of β-Hydroxy Nitriles, Amides, and Esters. Chemistry Letters, 2005.
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114. Lam, H. W., Joensuu, P.M., Murray, G.J., Fordyce, E.A.F., Prieto, O. and Luebbers, T. (2006) Diastereoselective Cobalt-Catalyzed Reductive Aldol Cyclizations Using Diethylzinc as the Stoichiometric Reductant. Organic Letters, 8, 3729.
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117. For palladium catalyzed reductive aldol reaction, see: Kiyooka, S.I., Shimizu, A. and Torii, S. (1998) A Mild Aldol Reaction of Aryl Aldehydes through Palladium-Catalyzed Hydrosilation of α,β-Unsaturated Carbonyl Compounds with Trichlorosilane. Tetrahedron Letters, 39, 5237.
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119. Chiu, P. (2004) Organosilanes in Copper-Mediated Conjugate Reductions and Reductive Aldol Reactions. Synthesis, 13, 2210.
120. For copper-promoted reductive intramolecular Henry reaction, see: Chung, W.K. and Chiu, P. (2005) Reductive Intramolecular Henry Reactions Induced by Stryker's Reagent. Synlett, 1, 55.
121. For copper-promoted and catalyzed reductive cyclizations of α, β-acetylenic ketones tethered to ketones, see: Chiu, P. and Leung, S.K. (2004) Stoichiometric and Catalytic Reductive Aldol Cyclizations of Alkynediones Induced by Stryker's Reagent. Chemical Communications, 2308.
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