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Enantioselective copper-catalyzed conjugate addition to trisubstituted cyclohexenones: construction of stereogenic quaternary centers

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Published in Angewandte Chemie: International Edition. 2005, vol. 44, no. 9, p. 1376-1378
Abstract Trimethyl- and triethylaluminum undergo enantioselective conjugate addition to 3- and 2-substituted cyclohexenones in the presence of catalytic amounts of a Cu salt and a phosphoramidite ligand L* (see scheme). Thus, chiral quaternary centers can be built with up to 96.6 % ee. Functionalized enones lead to bicyclic structures by a subsequent aldol reaction.
Keywords AluminumAsymmetric catalysisConjugate additionEnonesPhosphoramidite ligands
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PMID: 15666416
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VUAGNOUX-D'AUGUSTIN DE, Magali, PALAIS, Laetitia, ALEXAKIS, Alexandre. Enantioselective copper-catalyzed conjugate addition to trisubstituted cyclohexenones: construction of stereogenic quaternary centers. In: Angewandte Chemie: International Edition, 2005, vol. 44, n° 9, p. 1376-1378. https://archive-ouverte.unige.ch/unige:8176

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Deposited on : 2010-06-21

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