Formation of quaternary stereogenic centers by NHC-Cu-catalyzed asymmetric conjugate addition reactions with Grignard reagents on polyconjugated cyclic enones. - Université Clermont Auvergne Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2012

Formation of quaternary stereogenic centers by NHC-Cu-catalyzed asymmetric conjugate addition reactions with Grignard reagents on polyconjugated cyclic enones.

Résumé

The copper-catalyzed conjugate addition of various Grignard reagents to polyconjugated enones (dienone and enynone derivatives) is reported. The catalyst system, composed of copper triflate and an NHC ligand, led to the unusual selective formation of the 1,4-addition products. This reaction allows for the creation of all-carbon chiral quaternary centers with enantiomeric excesses up to 99%. The remaining unsaturation on the 1,4 adducts give access to valuable synthetic transformations.

Domaines

Catalyse

Dates et versions

hal-00875596 , version 1 (22-10-2013)

Identifiants

Citer

Matthieu Tissot, Daniele Poggiali, Hélène Henon, Daniel Müller, Laure Guénée, et al.. Formation of quaternary stereogenic centers by NHC-Cu-catalyzed asymmetric conjugate addition reactions with Grignard reagents on polyconjugated cyclic enones.. Chemistry - A European Journal, 2012, 18 (28), pp.8731-47. ⟨10.1002/chem.201200502⟩. ⟨hal-00875596⟩
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