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Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminum to β,γ-Unsaturated α-Ketoamides: Efficient Access to γ-Methyl-Substituted Carbonyl Compounds

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Published in Angewandte Chemie: International Edition. 2013, vol. 52, no. 48, p. 12701-12704
Abstract Picture perfect: By using the reagent trimethylaluminium and β,γ-unsaturated α-ketoamides, 1,4-adducts were obtained with perfect 1,4-regioselectivity and good to excellent yields and ee values. The potential synthetic utility of the methodology was highlighted by preparation of γ-methyl-substituted carbonyls, key synthons to many natural products. binap=2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, TC=thiophene carboxylate.
Keywords Asymmetric catalysisCopperEnantioselectivityNatural productsSynthetic methods
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Other version: http://doi.wiley.com/10.1002/anie.201306541
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CONTAL, Sylvie, GREMAUD, Ludovic, ALEXAKIS, Alexandre. Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminum to β,γ-Unsaturated α-Ketoamides: Efficient Access to γ-Methyl-Substituted Carbonyl Compounds. In: Angewandte Chemie: International Edition, 2013, vol. 52, n° 48, p. 12701-12704. https://archive-ouverte.unige.ch/unige:31130

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Deposited on : 2013-11-19

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