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Synthesis and Molecular Modeling Studies of SYNPHOS ® , a New, Efficient Diphosphane Ligand For Ruthenium‐Catalyzed Asymmetric Hydrogenation
Author(s) -
Paule Sébastien Duprat de,
Jeulin Séverine,
RatovelomananaVidal Virginie,
Genêt JeanPierre,
Champion Nicolas,
Dellis Philippe
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200200634
Subject(s) - ruthenium , chemistry , asymmetric hydrogenation , ligand (biochemistry) , binap , catalysis , noyori asymmetric hydrogenation , enantioselective synthesis , dihedral angle , optically active , combinatorial chemistry , organic chemistry , molecule , biochemistry , hydrogen bond , receptor
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)