Rhodium-phosphine chiral hydrogenation catalysis of acetophenone

Details Rhodium-phosphine chiral hydrogenation catalysis of acetophenone Rhodium-phosphine chiral hydrogenation catalysis of acetophenone

1982-01-18

1984-04-03

Coughlan, Jr., Paul M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548502, 560 42, 560155, 562433, 562446, 562496, 564161, 564184, 564186, 564192, 568814, C07D20920, C07C 6513, C07C10104, C07C10300

Patent

active

044409362

ABSTRACT:
The chiral phosphine ligand (R)-1,2-bis(diphenylphosphino)-1-cyclohexylethane, when complexed to Rh(I), functions as a superior chiral hydrogenation catalyst. The chiral phosphine ligand is more stereochemically rigid than previous compounds; consequently, virtually optically pure materials can be produced from the chiral hydrogenation of prochiral compounds using the catalyst of this invention. This catalyst is especially useful in the chiral hydrogenation of alpha-acylamido acrylic acids.

REFERENCES:
patent: 3798241 (1974-03-01), Kagan et al.
patent: 3978101 (1976-08-01), Aviron-Violet
patent: 4008281 (1977-02-01), Knowles et al.
King et al., "1,2-Bis(diphenylphosphino)-1-phenylethane: A Chiral Ditertiary Phosphine Derived from Mandelic Acid Used as a Ligand in Asymmetric Homogeneous Hydrogenation Catalysts", J. Org. Chem., vol. 44, (1979), pp. 1729-1731.
Brown, et al.,--"R-Phenyl Bis Diphenylphosphinoethane; Structural Studies Pertaining to Rhodium--Catalysed Asymmetric Hydrogenation", Tet. Lett., No. 50, (1979), pp. 4859-4862.
Fryzuk, et al., "Asymmetric Synthesis: Production of Optically Active Amino Acids by Catalytic Hydrogenation," J. Am. Chem. Soc., vol. 100, (1978), pp. 6262-6267.
Halpern, et al., "Novel Coordination Chemistry and Catalytic Properties of Cationic 1,2-Bis(diphenylphosphino)etheranerhodium(I) Complexes", J. Am. Chem. Soc., vol. 99, (1977), pp. 8055-8057.
Halpern, et al., "Some Aspects of the Coordination Chemistry and Catalytic Properties of Cationic Rhodium-Phosphine Complexes", Adv. Chem. Ser., vol. 173, (1979), pp. 16-25.
Chan et al., "Intermediates in Homogeneous Catalytic Hydrogenation: The Crystal and Molecular Structure of the Methyl(Z)--Alpha--Acetamiaodicinnamate Adduct of 1,2--Bis(diphenylphosphino)ethanerhodium (I),", Inorg. Chim. Acta., vol. 37, (1979), pp. 1477-1479.
Vineyard et al., "Asymmetric Hydrogenation: Rhodium Chiral Bisphosphine Catalyst," J. Am. Chem. Soc., vol. 99, (1977), pp. 5946-5952.
Detellier et al., "Asymmetric Catalysis with Chiral Complexes of Rhodium--O--Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane. 6. On the Mechanism of Reduction of (E,Z)-alpha-Acylaminocinnamic Acids with Homogeneous Rhodium Catalysts", J. Am. Chem. Soc., vol. 100, (1978), pp. 7556-7561.
Kagan et al., "Asymmetric Catalytic Reduction with Transition Metal Complexes, A Catalytic System of Rhodium(I) with (-)-2,3-O-Isopropylidene-2,3--dihydroxy--1,4--bis(diphenylphosphino)butane , a New Chiral Diphosphine", J. Am. Chem. Soc., vol. 94, (1972), pp. 6429-6433.
Pino, et al., "Homogeneous Asymmetric Catalysis by Transition Metal Complexes", Fundamental Research in Homogeneous Catalysis, vol. 3, (1979), pp. 519-536.
Valentine, et al., "Asymmetric Synthesis", Synthesis, (1978), pp. 329-356.
Slack et al., ".sup.31 P NMR Studies of Catalytic Systems Containing Rhodium Complexes of Chelating Chiral and Achiral Diphosphines", Inorg. Chem., vol. 18, (1979), pp. 3125-3132.
Knowles, et al., "Use of X-Ray Crystal Structure in the Study of Asymmetric Catalysis", Fundamental Research in Homogeneous Catalysis, vol. 3, (1979), pp. 537-548.
Lauer et al., "Synthesis of Phellanphos, an Efficient Chiral 1,2-diphosphine for Asymmetric Catalysis", J. Organomet. Chem., vol. 177, (1979), pp. 309-312.

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