New Applications of Bis(oxazoline) Ligands in Catalysis: Asymmetric 1,2- and 1,4-Addition of ZnR2 to Carbonyl Compounds
- 1 December 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (26), 4259-4262
- https://doi.org/10.1021/ol016925g
Abstract
The enantioselective addition of ZnR2 to aldehydes (1,2) and cyclic enones (1,4) was accomplished using bis(oxazolines) as chiral ligands. The requirement for hydroxymethylene side chains in the ligands strongly suggests that bimetallic catalysts are decisive for high enantiocontrol in these additions.Keywords
This publication has 15 references indexed in Scilit:
- Highly active and enantioselective copper-catalyzed conjugate addition of diethylzinc to cyclohexenone using sugar derivative diphosphitesTetrahedron: Asymmetry, 2000
- Asymmetric, Catalytic Phenyl Transfer to Aldehydes: Enantioselective Synthesis of DiarylmethanolsPublished by Wiley ,2000
- Asymmetric conjugate addition of diethylzinc to chalcone catalyzed by nickel complexes containing derivatives of (1R,2S,3R)-3-mercaptocamphan-2-olTetrahedron: Asymmetry, 2000
- New Chiral Oxazoline-Phosphite Ligands for the Enantioselective Copper-Catalyzed 1,4-Addition of Organozinc Reagents to EnonesTetrahedron, 2000
- Highly Enantioselective Catalytic Conjugate Additions to CyclohexadienonesOrganic Letters, 1999
- Unexpected enhancement of enantioselectivity in copper(II) catalyzed conjugate addition of diethylzinc to cyclic enones with novel TADDOL phosphorus amidite ligandsTetrahedron: Asymmetry, 1998
- Asymmetric addition of diethylzinc to aromatic aldehydes using enantiomerically pure hydroxymethyl oxazoline ligandsTetrahedron: Asymmetry, 1993
- Intramolecular arylations of soft enolates catalyzed by zerovalent palladiumThe Journal of Organic Chemistry, 1988
- Chiral catalysts for the enantioselective addition of organometallic reagents to aldehydesTetrahedron Letters, 1987
- Copper-catalyzed acylation and conjugate addition of zinc homoenolate. Synthesis of 4- and 5-oxo estersJournal of the American Chemical Society, 1984