Synthesis and Molecular Modeling Studies of SYNPHOS®, a New, Efficient Diphosphane Ligand For Ruthenium-Catalyzed Asymmetric Hydrogenation

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 atropis...

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Veröffentlicht in:European journal of organic chemistry 2003-05, Vol.2003 (10), p.1931-1941
Hauptverfasser: Paule, Sébastien Duprat de, Jeulin, Séverine, Ratovelomanana-Vidal, Virginie, Genêt, Jean-Pierre, Champion, Nicolas, Dellis, Philippe
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Sprache:eng
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Zusammenfassung: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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200200634