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Formation of Quaternary Stereogenic Centers by NHC-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Polyconjugated Cyclic Enones

Authors
Mauduit, Marc
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 synthesisConjugate additionsCopperGrignard reagentsN-heterocyclic carbenes
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Other version: http://doi.wiley.com/10.1002/chem.201200502
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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. https://archive-ouverte.unige.ch/unige:21875

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Deposited on : 2012-07-18

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