Unexpected enhancement of enantioselectivity in copper(II) catalyzed conjugate addition of diethylzinc to cyclic enones with novel TADDOL phosphorus amidite ligands

Erik Keller, Jochen Maurer, Robert Naasz, Thomas Schader, Auke Meetsma, Ben L. Feringa

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

The copper(II) catalyzed enantioselective 1,4-addition reactions of diethylzinc to cyclic enones in the presence of novel phosphorus amidite ligands, easily prepared from α,α,α',α'-tetraphenyl-2,2'-dimethyl-1,3- dioxolane-4,5-dimethanol (TADDOL) derivatives, resulted in e.e.s up to 71% for cyclohexenone and up to 62% for cyclopentenone. A remarkable enhancement of enantioselectivity was observed upon the addition of powdered molecular sieves to the reaction mixture.
Original languageEnglish
Pages (from-to)2409-2413
JournalTetrahedron: asymmetry
Volume9
Issue number14
DOIs
Publication statusPublished - 17 Jul 1998

Keywords

  • copper

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