Enantioselective Tandem Michael Addition/H2-Hydrogenation Catalyzed by Ruthenium Hydride Borohydride Complexes Containing β-aminophosphine Ligands
- 18 December 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (2) , 516-517
- https://doi.org/10.1021/ja043782v
Abstract
A variety of ruthenium(II) catalyst precursors containing β-aminophosphine ligands and a borohydride ligand were found to be active for a one-pot, tandem asymmetric Michael addition/H2-hydrogenation reaction to give the chiral alcohol in excellent diastereomeric excess. The most effective catalyst is 4b, containing the (S)-binap ligand and (R,R)-Pnor ligand, derived from (1S,2R)-norephedrine.Keywords
This publication has 10 references indexed in Scilit:
- Catalytic Enantioselective Michael Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes Catalyzed by Well-Defined Chiral Ru Amido ComplexesJournal of the American Chemical Society, 2004
- Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexesCoordination Chemistry Reviews, 2004
- Highly Enantio‐ and Diastereoselective Organocatalytic Asymmetric Domino Michael–Aldol Reaction of β‐Ketoesters and α,β‐Unsaturated KetonesAngewandte Chemie International Edition in English, 2004
- Mechanism of Asymmetric Hydrogenation of Ketones Catalyzed by BINAP/1,2-Diamine−Ruthenium(II) ComplexesJournal of the American Chemical Society, 2003
- Enantioselective Michael Reaction Catalyzed by Well-Defined Chiral Ru Amido Complexes: Isolation and Characterization of the Catalyst Intermediate, Ru Malonato Complex Having a Metal−Carbon BondJournal of the American Chemical Society, 2003
- Mechanism of the Hydrogenation of Ketones Catalyzed by trans-Dihydrido(diamine)ruthenium(II) ComplexesJournal of the American Chemical Society, 2002
- trans-RuH(η-BH4)(binap)(1,2-diamine): A Catalyst for Asymmetric Hydrogenation of Simple Ketones under Base-Free ConditionsJournal of the American Chemical Society, 2002
- Metal−Ligand Bifunctional Catalysis: A Nonclassical Mechanism for Asymmetric Hydrogen Transfer between Alcohols and Carbonyl CompoundsThe Journal of Organic Chemistry, 2001
- Catalytic Cycle for the Asymmetric Hydrogenation of Prochiral Ketones to Chiral Alcohols: Direct Hydride and Proton Transfer from Chiral Catalysts trans-Ru(H)2(diphosphine)(diamine) to Ketones and Direct Addition of Dihydrogen to the Resulting Hydridoamido ComplexesJournal of the American Chemical Society, 2001
- Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of KetonesAngewandte Chemie International Edition in English, 2001