PipPhos and MorfPhos: Privileged Monodentate Phosphoramidite Ligands for Rhodium-Catalyzed Asymmetric Hydrogenation
- 5 January 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (3) , 943-951
- https://doi.org/10.1021/jo048374o
Abstract
A library of 20 monodentate phosphoramidite ligands has been prepared and applied in rhodium-catalyzed asymmetric hydrogenation. This resulted in the identification of two ligands, PipPhos and MorfPhos, that afford excellent and in several cases unprecedented enantioselectivities in the hydrogenation of N-acyldehydroamino acid esters, dimethyl itaconate, acyclic N-acylenamides, and cyclic N-acylenamides. In addition, a method for the parallel enantioselectivity determination of eight acylated amines is presented.Keywords
This publication has 61 references indexed in Scilit:
- Synthesis and application in asymmetric C–C bond formation of solution phase ligand libraries of monodentate phosphoramiditesOrganic & Biomolecular Chemistry, 2004
- Binaphthyldiamine-Based Diazaphospholidinesas a New Class of Chiral Monodentate P-LigandsSynthesis, 2003
- Highly Enantioselective Rhodium‐Catalyzed Hydrogenation of 2‐(2‐Methoxy‐2‐oxoethyl)acrylic Acid − A Convenient Access of Enantiomerically Pure Isoprenoid Building BlocksEuropean Journal of Organic Chemistry, 2003
- Chiral Phosphoric Acid Diesters as Ligands in Asymmetric Transition Metal Catalyzed HydrogenationChimia, 2003
- Selective Hydrogenation for Fine Chemicals: Recent Trends and New DevelopmentsAdvanced Synthesis & Catalysis, 2003
- Large-Scale Computational Modeling of [Rh(DuPHOS)]+-Catalyzed Hydrogenation of Prochiral Enamides: Reaction Pathways and the Origin of EnantioselectionJournal of the American Chemical Society, 2000
- Highly Enantioselective Rh-Catalyzed Hydrogenation Reactions Based on Chiral Monophosphite LigandsPublished by Wiley ,2000
- Structures and Reaction Pathways in Rhodium(I)-Catalyzed Hydrogenation of Enamides: A Model DFT StudyJournal of the American Chemical Society, 1999
- A further synthesis of the corticosteroid side chain starting with a suitable 17-ketoneJournal of the Chemical Society, Perkin Transactions 1, 1985
- Asymmetric hydrogenationAccounts of Chemical Research, 1983