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Title

Formation of Quaternary Stereogenic Centers by NHC-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Polyconjugated Cyclic Enones
Authors
Tissot, Matthieu
Poggiali, Daniele
Henon, Hélène
Mueller, Daniel
Guenee, Laure
Mauduit, Marc
Alexakis, Alexandre
Published in Chemistry - A European Journal. 2012, vol. 18, no. 28, p. 8731-8747
Abstract 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.
Keywords Asymmetric synthesis — Conjugate additions — Copper — Grignard reagents — N-heterocyclic carbenes
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Structures
Faculté des sciences / Section de chimie et biochimie / Département de chimie minérale, analytique et appliquée
Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
Citation
(ISO format) 		TISSOT, Matthieu et al. Formation of Quaternary Stereogenic Centers by NHC-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Polyconjugated Cyclic Enones. In: Chemistry - A European Journal, 2012, vol. 18, n° 28, p. 8731-8747. doi: 10.1002/chem.201200502 https://archive-ouverte.unige.ch/unige:21875

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Deposited on : 2012-07-18

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