Synthesis and Molecular Modeling Studies of SYNPHOS®, a New, Efficient Diphosphane Ligand For Ruthenium‐Catalyzed Asymmetric Hydrogenation
- 5 May 2003
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2003 (10) , 1931-1941
Abstract
A new, optically active, atropisomeric diphosphane ligand, (2,3,2′,3′‐tetrahydro‐5,5′‐bi(1,4‐benzodioxin)‐6,6′‐diyl)bis‐(diphenylphosphane) (SYNPHOS®), has been synthesized, characterized, and used in ruthenium‐catalyzed asymmetric hydrogenations. This new ligand has been compared with other atropisomeric diphosphanes (BINAP and MeO‐BIPHEP) with respect to their dihedral angles calculated by molecular modeling and the enantioselectivity of their ruthenium‐mediated hydrogenation reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)Keywords
This publication has 42 references indexed in Scilit:
- Asymmetric Catalysis: Science and Opportunities (Nobel Lecture) Copyright© The Nobel Foundation 2002. We thank the Nobel Foundation, Stockholm, for permission to print this lecture.Angewandte Chemie International Edition, 2002
- Recent studies on asymmetric hydrogenation. New catalysts and synthetic applications in organic synthesis2002
- Synthetic applications of the ruthenium-catalyzed hydrogenation via dynamic kinetic resolutionCanadian Journal of Chemistry, 2000
- New Developments in Chiral Ruthenium (II) Catalysts for Asymmetric Hydrogenation and Synthetic Applications1996
- Palladium-catalyzed asymmetric arylation of 2,3-dihydrofuran with phenyl triflate. A novel asymmetric catalysis involving a kinetic resolution processOrganometallics, 1993
- Selective ortho lithiation of (2,5-dimethoxyphenyl)diphenylphosphine oxide and trapping of the resulting aryllithium with electrophilesThe Journal of Organic Chemistry, 1991
- Asymmetric hydrogenation of prochiral alkenes catalysed by ruthenium complexes of (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthylJournal of the Chemical Society, Perkin Transactions 1, 1989
- Asymmetrische Katalysen, V. Enantioselektive Aminosäuresynthese durch Hydrierung prochiraler Olefine mit Rh‐Komplexen des neuen optisch aktiven chelatbildenden Phosphans NorphosEuropean Journal of Inorganic Chemistry, 1981
- Resolutions using metal complexes. Synthesis, separation into diastereoisomers, and resolution of o-phenylenebis(methylphenylphosphine) using palladium complexes containing optically active ortho-metalated dimethyl(.alpha.-methylbenzyl)aminesJournal of the American Chemical Society, 1979
- Chiral metal complexes. 4. Resolution of racemic tertiary phosphines with chiral palladium(II) complexes. The chemistry of diastereomeric phosphine palladium(II) species in solutionJournal of the American Chemical Society, 1977