First Examples of Improved Catalytic Asymmetric C−C Bond Formation Using the Monodentate Ligand Combination Approach
- 22 July 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (17) , 3111-3113
- https://doi.org/10.1021/ol035106o
Abstract
[reaction: see text] Using a combination of chiral monodentate phosphoramidite ligands in the rhodium-catalyzed conjugate addition of boronic acids to three different substrates, we have shown for the first time that the ligand combination approach is applicable for C-C bond formation. Chiral catalysts based on hetero-combinations of ligands are found to be more effective than the homo-combinations. (31)P NMR experiments show that the hetero-combinations are formed in excess over the homo-combinations.Keywords
This publication has 17 references indexed in Scilit:
- Highly Enantioselective Conjugate Addition of Dialkylzinc Reagents to Acyclic Nitroalkenes: A Catalytic Route to β2-Amino Acids, Aldehydes, and AlcoholsJournal of the American Chemical Society, 2003
- Improving conversion and enantioselectivity in hydrogenation by combining different monodentate phosphoramidites; a new combinatorial approach in asymmetric catalysisElectronic supplementary information (ESI) available: Experimental details. See http://www.rsc.org/suppdata/ob/b3/b302097e/Organic & Biomolecular Chemistry, 2003
- A New Principle in Combinatorial Asymmetric Transition‐Metal Catalysis: Mixtures of Chiral Monodentate P LigandsAngewandte Chemie International Edition in English, 2003
- Monodentate Phosphoramidites: A Breakthrough in Rhodium‐Catalysed Asymmetric Hydrogenation of OlefinsAdvanced Synthesis & Catalysis, 2003
- Highly Enantioselective Rhodium-Catalyzed Hydrogenation of β-Dehydroamino Acid Derivatives Using Monodentate PhosphoramiditesJournal of the American Chemical Society, 2002
- Catalytic Enantioselective Synthesis of (−)-Prostaglandin E1 Methyl Ester Based on a Tandem 1,4-Addition−Aldol ReactionThe Journal of Organic Chemistry, 2002
- The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated AldehydesJournal of the American Chemical Society, 2002
- Rhodium(I)-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated AmidesThe Journal of Organic Chemistry, 2001
- Highly Enantioselective Rhodium-Catalyzed Hydrogenation with Monodentate LigandsJournal of the American Chemical Society, 2000
- Asymmetric Conjugate 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Esters Catalyzed by Rhodium(I)/(S)-binapThe Journal of Organic Chemistry, 2000