Highly Enantioselective Copper-Catalyzed Conjugate Addition of Diethylzinc to Enones Using Chiral Spiro Phosphoramidites as Ligands
- 11 January 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (4) , 1582-1584
- https://doi.org/10.1021/jo026611m
Abstract
Novel monodentate chiral spiro phosphoramidite ligands have been readily synthesized in good yields from enantiomerically pure 1,1‘-spirobiindane-7,7‘-diol. The new ligands were highly efficient in the copper-catalyzed conjugate addition of Et2Zn to enones with up to 98% enantiomeric excess.Keywords
This publication has 18 references indexed in Scilit:
- Highly efficient and practical resolution of 1,1′-spirobiindane-7,7′-diol by inclusion crystallization with N-benzylcinchonidinium chlorideTetrahedron: Asymmetry, 2002
- Copper-catalyzed conjugate addition on macrocyclic, cyclic, and acyclic enones with a chiral phosphoramidite ligand having a C2-symmetric amine moietyTetrahedron: Asymmetry, 2002
- Copper-catalyzed enantioselective conjugate addition of diethylzinc to α,β-unsaturated carbonyl compounds using diphosphonites as chiral ligandsTetrahedron Letters, 2002
- Conjugate addition of diethylzinc to α,β-unsaturated lactones catalyzed by copper–phosphite complexesChemical Communications, 2000
- Enantioselective conjugate addition of diethylzinc to cyclic enones with chiral aryl diphosphite-copper catalystsTetrahedron Letters, 1999
- Highly Enantioselective Catalytic Conjugate Additions to CyclohexadienonesOrganic Letters, 1999
- 1,1′-Spirobiindane-7,7′-diol: a novel, C2-symmetric chiral ligandTetrahedron: Asymmetry, 1999
- Highly Enantioselective Catalytic Conjugate Addition and Tandem Conjugate Addition–Aldol Reactions of Organozinc ReagentsAngewandte Chemie International Edition in English, 1997
- Enantioselective Conjugate Addition of Dialkylzinc Reagents to Cyclic and Acyclic Enones Catalyzed by Chiral Copper Complexes of New Phosphorus AmiditesAngewandte Chemie International Edition in English, 1996
- Asymmetric conjugate additionChemical Reviews, 1992