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Chromium-Catalyzed Homoaldol Equivalent Reaction Employing a Nucleophilic Propenyl Acetate

Jun Yong Kang and Brian T. Connell*

*Texas A&M University, Department of Chemistry, P.O. Box 30012, College Station, Texas 77842-3012, Email: connellchem.tamu.edu

J. Y. Kang, B. T. Connell, J. Am. Chem. Soc., 2010, 132, 7826-7827.

DOI: 10.1021/ja910057g (free Supporting Information)


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Abstract

A highly regioselective chromium-catalyzed addition of 3-bromopropenyl acetate as a masked homoenolate nucleophile to aromatic, aliphatic, and α,β-unsaturated aldehydes allows the synthesis of homoaldol equivalent products in very good yields. The vinyl acetate adducts are easily hydrolyzed with mild base to provide formal homoaldol adducts, or transformed to other more functionalized products.

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Key Words

γ-hydroxy aldehydes, allylation, Nozaki-Hiyama Coupling, manganese


ID: J48-Y2010-1580