Iridium-N,P-Ligand-Catalyzed Enantioselective Hydrogenation of Diphenylvinylphosphine Oxides and Vinylphosphonates
- 22 May 2009
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 131 (23), 8285-8289
- https://doi.org/10.1021/ja901437t
Abstract
Diphenylvinylphosphine oxides and di- and trisubstituted vinylphosphonates have been employed as substrates in iridium-catalyzed asymmetric hydrogenations. Complete conversions and excellent enantioselectivities (up to and above 99% ee) were observed for a range of substrates with both aromatic and aliphatic groups at the prochiral carbon. We have also hydrogenated electron-deficient carboxyethylvinylphosphonates with excellent stereoselectivity (up to and above 99% ee). The hydrogenated products of both classes of substrates are synthetically useful intermediates.Keywords
This publication has 80 references indexed in Scilit:
- Synthesis of β-Aminophosphonates and -PhosphinatesChemical Reviews, 2005
- Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological ActivityChemical Reviews, 2004
- Metal‐Catalyzed Cross‐Coupling ReactionsPublished by Wiley ,2004
- Synthetic and structural chemistry of enantiomerically pure 1-phenyl-2-carboxyethylphosphonic acid and its derivativesElectronic supplementary information (ESI) available: Tables S1–6. See http://www.rsc.org/suppdata/nj/b1/b111244a/New Journal of Chemistry, 2002
- Tuning the Reversible Binding of NO to Iron(II) Aminocarboxylate and Related Complexes in Aqueous SolutionEuropean Journal of Inorganic Chemistry, 2001
- Synthesis and characterization of Co3(O2CCH2CH2PO3)2·6H2O, a metal carboxylate–phosphonate with a framework structureChemical Communications, 1998
- Acylphosphorus, -Arsenic, -Antimony and -Bismuth FunctionsPublished by Elsevier ,1995
- Use of Layered Metal Phosphonates for the Design and Construction of Molecular MaterialsChemistry of Materials, 1994
- Proton conductivity of zirconium carboxy n-alkyl phosphonates with an α-layered structureSolid State Ionics, 1991
- Complexation, luminescence, and energy transfer of cerium(3+) with a series of multidentate aminophosphonic acids in aqueous solutionInorganic Chemistry, 1991