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Chiral Biphenyl Diphosphines for Asymmetric Catalysis: Stereoelectronic Design and Industrial Perspectives

Overview
Journal Proc Natl Acad Sci U S A
Specialty Science
Date 2004 Mar 20
PMID 15031423
Citations 8
Authors
Severine Jeulin
Sebastien Duprat de Paule
Virginie Ratovelomanana-Vidal
Jean-Pierre Genet
Nicolas Champion
Philippe Dellis
Affiliations
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Abstract

Two original chiral diphosphines, SYNPHOS and DIFLUORPHOS, have been synthesized on multigram scales. Their steric and electronic profiles have been established in comparison with the commonly used 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl and 6,6'-dimethoxy-2,2'-bis(diphenylphosphino)-1,1'-biphenyl ligands. A screening study of the four ligands in Ru(II)-catalyzed asymmetric hydrogenation of prochiral ketones and olefins has been performed. It revealed that the stereoelectronic features of the ligand and the substrate deeply influenced the enantioselectivities obtained in asymmetric hydrogenation, SYNPHOS and DIFLUORPHOS being fully complementary in terms of enantioselectivity for this reaction.

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