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Scientific article
English

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

Published inAngewandte Chemie, vol. 52, no. 48, p. 12701-12704
Publication date2013
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 catalysis
  • Copper
  • Enantioselectivity
  • Natural products
  • Synthetic methods
Citation (ISO format)
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, 2013, vol. 52, n° 48, p. 12701–12704. doi: 10.1002/anie.201306541
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ISSN of the journal1433-7851
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Creation11/19/2013 9:22:00 AM
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