Optimization of asymmetric catalysts using achiral ligands: Metal geometry-induced ligand asymmetry

Citation
Tj. Davis et al., Optimization of asymmetric catalysts using achiral ligands: Metal geometry-induced ligand asymmetry, ORG LETT, 3(14), 2001, pp. 2161-2164
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
14
Year of publication
2001
Pages
2161 - 2164
Database
ISI
SICI code
1523-7060(20010712)3:14<2161:OOACUA>2.0.ZU;2-V
Abstract
[GRAPHICS] Traditionally, asymmetric catalysts have been optimized by modification of resolved chiral ligands, In this Letter, we optimize the asymmetric additio n of diethylzine to aldehydes by modification of achiral methylene bis(phen ol) ligands, Upon coordination of the substrate, the achiral ligand becomes asymmetric, a concept termed Metal Geometry-induced Ligand Asymmetry, The enantioselectivity of the catalyst formed from a single resolved ligand and several achiral ligands ranged from 9% (R) to 83% (S).