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