Ru(II)-Catalyzed Enantioselective Transfer Hydrogenation of α-Ketophosphonates: Straightforward Access to Valuable Chiral α-Hydroxy Phosphonates
- 20 November 2023
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 88 (23) , 16661-16665
Abstract
Asymmetric transfer hydrogenation (ATH) is arguably one of the most powerful tools for the synthesis of chiral compounds. Despite tremendous advances in this field, the reduction of α-ketophosphonates remains largely unexplored. Herein, we report an efficient Ru-catalyzed ATH on a broad range of α-ketophosphonates. Compared with existing methods, our approach offers as advantages mild conditions, operational simplicity, limited waste generation, broad substrate scope (26 examples), good to excellent yields (75-93%), and excellent levels of stereoinduction (from 90% to >99% ee).Keywords
Funding Information
- Association Nationale de la Recherche et de la Technologie (2021/0582)
- Phost'in Therapeutics
This publication has 51 references indexed in Scilit:
- Oxo-Tethered Ruthenium(II) Complex as a Bifunctional Catalyst for Asymmetric Transfer Hydrogenation and H2 HydrogenationJournal of the American Chemical Society, 2011
- Dynamic Kinetic Resolution: Asymmetric Transfer Hydrogenation of α-Alkyl-Substituted β-KetoamidesOrganic Letters, 2009
- Asymmetric Hydrogenation of α‐Keto Phosphonates with Chiral Palladium CatalystsEuropean Journal of Organic Chemistry, 2009
- Asymmetric Transfer Hydrogenation of Ketones with Bifunctional Transition Metal-Based Molecular CatalystsAccounts of Chemical Research, 2007
- Antivaccinia Activities of Acyclic Nucleoside Phosphonate Derivatives in Epithelial Cells and Organotypic CulturesAntimicrobial Agents and Chemotherapy, 2002
- Role of alendronate and risedronate in preventing and treating osteoporosis.Cleveland Clinic Journal of Medicine, 2001
- Catalytic Concepts for the Enantioselective Synthesis ofα-Amino andα-Hydroxy PhosphonatesChemistry – A European Journal, 2000
- Novel Peptidyl Phosphorus Derivatives as Inhibitors of Human Calpain IJournal of Medicinal Chemistry, 1998
- Asymmetric Transfer Hydrogenation Catalyzed by Chiral Ruthenium ComplexesAccounts of Chemical Research, 1997
- Asymmetric synthesis of chiral, nonracemic dialkyl α‐hydroxyarylmethyl‐and α‐, β‐ and γ‐hydroxyalkylphosphonates from keto phosphonatesEuropean Journal of Organic Chemistry, 1995