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Formation of Quaternary Stereogenic Centers by Copper-Catalyzed Asymmetric Conjugate Addition Reactions of Alkenylaluminums to Trisubstituted Enones
Authors
Mueller, Daniel
Alexakis, Alexandre
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 Aluminum — Asymmetric synthesis — Conjugate addition — Copper — Phosphorous
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Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
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(ISO format) 		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. doi: 10.1002/chem.201302856 https://archive-ouverte.unige.ch/unige:30742

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Deposited on : 2013-10-28

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