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Synthesis of γ-hydroxy ketones and aldehydes

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