Formation of quaternary stereogenic centers by NHC-Cu-catalyzed asymmetric conjugate addition reactions with Grignard reagents on polyconjugated cyclic enones.
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.
Departement of Organic Chemistry, Université de Genève, 30 quai Ernest-Ansermet, 1211 Genève-4, Switzerland.
Matthieu
M
Tissot
Daniele
D
Poggiali
Hélène
H
Hénon
Daniel
D
Müller
Laure
L
Guénée
Marc
M
Mauduit
Alexandre
A
Alexakis