en
Scientific article
Letter
English

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

Published inTetrahedron letters, vol. 43, no. 44, p. 7887-7890
Publication date2002
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 catalysis
  • Enantioselectivity
  • Epimerization
  • Kinetic resolution
  • Michael addition
  • Phosphoramidites
Citation (ISO format)
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. doi: 10.1016/S0040-4039(02)01898-1
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Article (Published version)
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ISSN of the journal0040-4039
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