C2-Symmetric Diphosphinite Ligands Derived from Carbohydrates. The Strong Influence of Remote Stereocenters on Asymmetric Rhodium-Catalyzed Hydrogenation
- 30 September 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (22) , 7502-7510
- https://doi.org/10.1021/jo0496502
Abstract
Modular ligands of C2 symmetry (13a−e, 14a,b,d, and ent-9), systematically modified at positions 2 and 5, were easily prepared from d-glucosamine, d-glucitol, and tartaric acid, respectively. The application of these ligands in the rhodium-catalyzed hydrogenation of methyl acetamidoacrylate, methyl acetamidocinnamate, and dimethyl itaconate shows that both the configuration and the substituents at positions 2 and 5 of the tetrahydrofuran backbone have a strong influence on the enantioselectivty of the processes.This publication has 28 references indexed in Scilit:
- Asymmetric hydroformylation of styrene catalyzed by carbohydrate diphosphite-Rh(I) complexesNew Journal of Chemistry, 2002
- Chiral Diphosphites Derived from d-Glucose: New Highly Modular Ligands for the Asymmetric Catalytic HydrogenationThe Journal of Organic Chemistry, 2002
- Water-Soluble Organometallic Catalysts from Carbohydrates. 1. Diphosphinite−Rh ComplexesOrganic Letters, 1999
- ORTEP-3 for Windows - a version ofORTEP-III with a Graphical User Interface (GUI)Journal of Applied Crystallography, 1997
- Carbohydrate Phosphinites as Practical Ligands in Asymmetric Catalysis: Electronic Effects and Dependence of Backbone Chirality in Rh-Catalyzed Asymmetric Hydrogenations. Synthesis of R- or S-Amino Acids Using Natural Sugars as Ligand PrecursorsThe Journal of Organic Chemistry, 1997
- Role of Electronic Asymmetry in the Design of New Ligands: The Asymmetric Hydrocyanation ReactionJournal of the American Chemical Society, 1996
- Ligand Electronic Effects in Asymmetric Catalysis: Enhanced Enantioselectivity in the Asymmetric Hydrocyanation of VinylarenesJournal of the American Chemical Society, 1994
- Electronic effects in asymmetric catalysis: Enantioselective carbon-carbon bond forming processesPublished by Walter de Gruyter GmbH ,1994
- Tailored ligands for asymmetric catalysis: the hydrocyanation of vinyl arenesJournal of the American Chemical Society, 1992
- Asymmetric Synthesis using Organometallic CatalystsPublished by Elsevier ,1982