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Copper catalysed asymmetric conjugate addition of trialkylaluminuim reaggents to trisubstituted enones: construction of chiral quaternary centers

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Published in Chemistry - A European Journal. 2007, vol. 13, no. 34, p. 9647-9662
Abstract The Cu-catalyzed enantioselective conjugate addition of dialkylzinc to bis-alpha,beta-unsaturated carbonyl compounds followed by the intramolecular trapping of the zinc enolate in the presence of chiral phosphoramidite ligands was investigated. Cyclic and heterocyclic compounds with multichiral centers were formed as a mixture of two diastereomers with excellent diastereoselectivities (up to 99:1) and enantioselectivities (up to 94 % ee, ee=enantiomeric excess). The stereochemistry was determined to be trans,trans for the major products and trans,cis for the minor products. The absolute configuration of the cyclic compounds was assigned by comparison with the analogous adduct derived from trans-3-nonen-2-one and Et(2)Zn or the adduct obtained through conjugate addition of Me(2)Zn to trans-1-phenyl-non-2-en-1-one. Further transformation of these cyclic products into more complex compounds is under investigation in our laboratory.
Keywords CopperCyclizationEnolatesMichael additionSelectivity
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VUAGNOUX-D'AUGUSTIN DE, Magali, ALEXAKIS, Alexandre. Copper catalysed asymmetric conjugate addition of trialkylaluminuim reaggents to trisubstituted enones: construction of chiral quaternary centers. In: Chemistry - A European Journal, 2007, vol. 13, n° 34, p. 9647-9662. https://archive-ouverte.unige.ch/unige:8127

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Deposited on : 2010-06-21

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