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Formation of Quaternary Stereogenic Centers by Copper-Catalyzed Asymmetric Conjugate Addition Reactions of Alkenylaluminums to Trisubstituted Enones

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Published in Chemistry - A European Journal. 2013, vol. 19, no. 45, p. 15226-15239
Abstract Alkenylaluminums undergo asymmetric copper-catalyzed conjugate addition (ACA) to β-substituted enones allowing the formation of stereogenic all-carbon quaternary centers. Phosphinamine–copper complexes proved to be particularly active and selective compared with phosphoramidite ligands. After extensive optimization, high enantioselectivities (up to 96 % ee) were obtained for the addition of alkenylalanes to β-substituted enones. Two strategies for the generation of the requisite alkenylaluminums were explored allowing for the introduction of aryl- and alkyl-substituted alkenyl nucleophiles. Moreover, alkyl-substituted phosphinamine (SimplePhos) ligands were identified for the first time as highly efficient ligands for the Cu-catalyzed ACA.
Keywords AluminumAsymmetric synthesisConjugate additionCopperPhosphorous
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Other version: http://doi.wiley.com/10.1002/chem.201302856
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MUELLER, Daniel, ALEXAKIS, Alexandre. Formation of Quaternary Stereogenic Centers by Copper-Catalyzed Asymmetric Conjugate Addition Reactions of Alkenylaluminums to Trisubstituted Enones. In: Chemistry - A European Journal, 2013, vol. 19, n° 45, p. 15226-15239. https://archive-ouverte.unige.ch/unige:30742

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Deposited on : 2013-10-28

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