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Epimerization and kinetic resolution in copper-catalyzed enantioselective 1,4-additions of organozinc reagents to 6-substituted cyclohex-2-enones

Authors
Mediavilla Urbaneja, Laura
Krause, Norbert
Published in Tetrahedron Letters. 2002, vol. 43, no. 44, p. 7887-7890
Abstract Enantioselective 1,4-addition reactions of diethyl-, dimethyl-, and di-n-butylzinc to 6-methylcyclohex-2-enone (1) and 6-t-butylcyclohex-2-enone (4), catalyzed by Cu(OTf)2 and phosphoramidites L1–L4 were examined. The additions to enone 1 proceeded with high enantioselectivity; by acid- or base-catalyzed epimerization, adduct (S,S)-2 can be obtained from racemic 1 in diastereo- and enantiomerically pure form. In contrast, Michael additions to substrate 4 were rather slow and could be used for the kinetic resolution of the enone.
Keywords Copper catalysisEnantioselectivityEpimerizationKinetic resolutionMichael additionPhosphoramidites
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MEDIAVILLA URBANEJA, Laura, ALEXAKIS, Alexandre, KRAUSE, Norbert. Epimerization and kinetic resolution in copper-catalyzed enantioselective 1,4-additions of organozinc reagents to 6-substituted cyclohex-2-enones. In: Tetrahedron Letters, 2002, vol. 43, n° 44, p. 7887-7890. https://archive-ouverte.unige.ch/unige:8093

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Deposited on : 2010-06-21

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