New chiral ditertiary phosphines as ligands in homogeneous catalysts for the asymmetric hydrogenation of olefins

Conference · Wed Aug 01 04:00:00 EDT 1979 · Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States)

OSTI ID:5678514

Vastag, S ^[1]; Marko, L; Bakos, J; King, R B; Hoff, C D

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1. Univ. of Chemical Engineering, Veszprem, Hungary

The search for new chiral ligands to use in asymmetric homogeneous catalysis is motivated in part by the need to use efficiently both material and energy resources. Such chiral catalysts offer in principle a means for highly specific conversions of achiral substrates to chiral products. Such conversions are of potential importance to the industrial production of useful chiral compounds such as drugs, vitamins, flavorings, and fragrances. The economic advantages attendant with such selectivity are demonstrated by Monsanto's industrial production of the Parkinson's disease drug L-DOPA. Since the original work by Horner and by Knowles and Sabacky in 1968 in which optical yields up to 15% were obtained in the hydrogenation of various prochiral olefins catalyzed by a rhodium complex of methylphenyl-n-propylphosphine, research in this area has rapidly proliferated. Optical yields approaching 100% in the hydrogenation of amino acid precursors have now been obtained in several laboratories. The high optical yields obtained in asymmetric hydrogenations of prochiral acylamido cinnamic acid derivatives using rhodium complexes of these chiral ditertiary phosphines suggests the particular efficacy of ditertiary phosphines forming a rigid chelate ring in maximizing the enantioselectivity of such reactions.

• OSTI ID: 5678514
• Report Number(s): CONF-790917-(Vol.24)(No.3)
• Conference Information: Journal Name: Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States) Journal Volume: 24:3
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKENES
AMINO ACIDS
CARBOXYLIC ACIDS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
DOPA
ELEMENTS
ENANTIOMORPHS
HYDROCARBONS
HYDROGENATION
HYDROXY ACIDS
LIGANDS
METALS
ORGANIC ACIDS
ORGANIC COMPOUNDS
PHOSPHINES
PHOSPHORUS COMPOUNDS
PLATINUM METALS
REFRACTORY METALS
RHODIUM
STEREOCHEMISTRY
TRANSITION ELEMENTS