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

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

Samenvatting

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.

OrganisatieHanzehogeschool Groningen
LectoraatBio Refinery
Gepubliceerd inTetrahedron: asymmetry Elsevier, Vol. 9, Uitgave: 14, Pagina's: 2409-2413
Datum1998-07-17
TypeArtikel
ISSN0957-4166
DOI10.1016/S0957-4166(98)00240-7
TaalEngels

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