Organic compounds -- part of the class 532-570 series – Organic compounds – Heavy metal containing
Patent
1995-05-18
1997-01-21
Springer, David B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heavy metal containing
C07F 1500
Patent
active
055961134
ABSTRACT:
.beta.- or .gamma.-Ketoesters and .beta.- or .gamma.-ketoamides are asymmetrically reduced with a Ru(II)-BINAP derived catalyst at about 40.degree. C. and about 50 N/mm.sup.2 of hydrogen in the presence of a strong acid.
REFERENCES:
patent: 4933482 (1990-06-01), Sayo et al.
patent: 4954644 (1990-09-01), Sayo et al.
"BINAP: An Efficient Chiral Element for Asymmetric Catalysis", Noyori, et al., Acc. Chem. Res., vol. 23, pp. 345-350 (1990).
"Convenient Preparation of Binap-Ruthenium(II) Complexes Catalyzing Asymmetric Hydrogenation of Functionalized Ketones", Kitamura, et al., Tetrahedron Letters, vol. 32(33), pp. 4163-4166 (1991).
"Enantioselective Reduction of .beta.-Keto Esters", Taber, et al., Tetrahedron Letters, vol. 32(34), pp. 4227-4230 (1991).
"Total Synthesis of (-)-Colletol", Keck and Murry, J. Org. Chem., vol. 56, pp. 6606-6611 (1991).
"Asymmetric Hydrogenation of .beta.-Keto Carboxylic Esters. A Practical, Purely Chemical Access to Beta-Hydroxy Esters in High Enantiomeric Purity", Noyori, et al., J. Am. Chem. Soc., vol. 109, pp. 5856-5858 (1987).
"Studies Relating to the Synthesis of the Immunosuppressive Agent FK-506: Coupling of Fragments via a Stereoselective Trisubstituted Olefin Forming Reaction Sequence", Jones, et al., J. Org. Chem., vol. 54, pp. 17-19 (1989).
"A Practical Asymmetric Synthesis of Carnitine", Kitamura, et al., Tetrahedron Letters, vol. 29(13), pp. 1555-1556 (1988).
"Synthesis of Statine and its Analogues by Homogeneous Asymmetric Hydrogenation", Nishi, et al., Tetrahedron Letters, vol. 29(48), pp. 6327-6330 (1988).
"Structural and Synthetic Studies of the Spore Germination Autoinhibitor Gloeosporone", Schreiber, et al., J. Am. Chem. Soc., vol. 110(18), pp. 6210-6218 (1988).
"Synthesis of Novel Chiral Ruthenium Complexes of 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl and their Use as Asymmetric Catalysts", Ikariya, et al., J. Chem. Soc., Chem. Commun., pp. 922-924 (1985).
"Formation of a Trimethyldihydroperimidinium Cation from Proton Sponge [1,8-Bis(dimethylamino)naphthalene] during Base-promoted Reactions of Rhodium and Ruthenium Complexes", Gamage, et al., J. Chem. Soc., Chem. Commun., pp. 894-895 (1987).
"Synthesis, Characterization and Reactivity of some Mono- and Dinuclear Chlororuthenium Complexes Containing Chelating Ditertiary Phosphines (P--P) with P--P:Ru=1", Joshi, et al., Inorg. Chimica Acta, 198-200, pp. 283-296 (1992).
"Enantioselective Synthesis of 4-Substituted .gamma.-Lactones", Ohkuma, et al., Tet. Ltrs., vol. 31(38), pp. 5509-5512 (1990).
"Characterization and Properties of the Dinuclear Ruthenium Molecular Hydrogen Complex [(.eta..sup.2 -H.sub.2)(dppb)Ru(.mu.-Cl).sub.3 RuCl(dppb)]; dppb=Ph.sub.2 P(CH.sub.2).sub.4 PPh.sub.2 ", Joshi and James, J. Chem. Soc., Chem. Commun., pp. 1785-1786 (1989).
"Enantioselective Ru-Mediated Synthesis of (-)-Indolizidine 223AB", Taber, et al., J. Org. Chem., vol. 57, pp. 5990-5994 (1992).
"Cyclopentane Construction with Control of Side Chain Configuration: Enantioselective Synthesis of (+)-Brefeldin A", Taber, et al., J. Am. Chem. Soc., vol. 113, pp. 6639-6645 (1991).
"Activation of Dihydrogen by Ruthenium(II)-Chelating Phosphine Complexes, and Activation of Dioxygen by Ruthenium(II) Porphyrin Complexes: An Update", James, et al., Journal Molecular Catalysis, vol. 41, pp. 147-161 (1987).
"Asymmetric Hydrogenation of 3-Oxo Carboxylates Using Binap-Ruthenium Complexes: (R)-(-)-Methyl 3-Hydroxybutanoate", Kitamura, et al., Org. Syn., vol. 71, pp. 1-13 (1992).
"Molecular Dihydrogen and Hydrido Derivatives of Ruthenium(II) Complexes Containing Chelating Ferrocenyl-Based Tertiary Phosphine Amine Ligands and/or Monodentate Tertiary Phosphine Ligands", Hampton, et al., Inorg. Chem., vol. 31, pp. 5509-5520 (1992).
"BINAP-Ruthenium(II) Dicarboxylate Complexes: New, Highly Efficient Catalysts for Asymmetric Hydrogenations", Ohta, et al., Inorg. Chem., vol. 27, pp. 566-569 (1988).
"Characterization and Reactivity of Di-.mu.-chloro-tetrahydridotetrakis-(triarylphosphine)-diruthenium(III) Complexes, Ru.sub.2 H.sub.4 Cl.sub.2 (PR.sub.3).sub.4 ", Dekleva, et al., Inorg. Chimica Acta, vol. 100, pp. 49-56 (1985).
"Trichloro-Bridged Diruthenium(I,III) Complexes: Preparation, Properties, and X-ray Structure of Ru.sub.2 Cl.sub.5 (chiraphos).sub.2 (chiraphos=2(S), 3(S)-Bis(diphenylphosphino)butane)", Thorburn, et al., Inorg. Chem., vol. 25, pp. 234-240 (1986).
"The Dichlorobis(triphenylphosphine)ruthenium(II) Dimer", James, et al., Inorg. Chimica Acta, vol. 29, pp. L237-L-238 (1978).
"Molecular-Hydrogen, Nitrogen and Monohydride Derivatives of the Structurally Characterized Dichloro)o-diphenylphosphino-N,N-dimethylaniline)[tris(p-tolyl)phosphine]r uthenium(II) Complex", Mudalige, et al., J. Chem. Soc., Chem. Commun., pp. 830-832 (1993).
"Highly Stereoselective Asymmetric Hydrogenation of 2-Benzamidomethyl-3-oxobutanoate Catalysed by Cationic binap-Ruthenium(II) Complexes.dagger.", Mashima, et al., J. Chem. Soc., Chem. Commun., No. 9, pp. 609-610 (1991).
"Asymmetric Hydrogenation of Unsaturated Carbonyl Compounds Catalyzed by BINAP-Ru(II) Complexes. Enantioselective Synthesis of .gamma.-Butyrolactones and Cyclopentanones", Ohta, et al., Tet. Ltrs., vol. 33(5), pp. 635-638 (1992).
"Synthesis of New Cationic BINAP-Ruthenium(II)Complexes and their Use in Asymmetric Hydrogenation [BINAP=2,2'-bis(diphenylphosphino)-1,1'binaphthyl]", Mashima, et al., J. Chem. Soc., Chem. Commun., pp. 1208-1210 (1989).
"Stereochemistry and Mechanism of the Asymmetric Hydrogenation of Unsaturated Carboxylic Acids Catalyzed by BINAP-Ruthenium(II) Dicarboxylate Complexes", Ohta, et al., Tet. Ltrs., vol. 31(49), pp. 7189-7192 (1990).
Takasago Int'l. Corp., "Asymmetric Synthesis: Asymmetric Hydrogenation Using BINAP-Complex Catalysts" (1993) Rockleigh N.J. 07647.
"A Molecular Dihydrogen Moiety within Dimeric Chlorohydrido(tertiary phosphine) Ruthenium Complexes", Hampton, et al., Inorg. Chimica Acta, vol. 145 pp. 165-166 (1988).
"Chemistry of the Transition Elements", Cotton and Wilkinson, Advance Inorg. Chem., 5 Edition, Wiley Inter. Sci., pp. 878-900 (1988).
"Asymmetric Catalysis by Chiral Metal Complexes", Noyori, Chemtech, pp. 360-367 (Jun. 1992).
"Homogeneous Asymmetric Hydrogenation of Functionalized Ketones", Kitamura, et al., J. Am. Chem. Soc., vol. 110, pp. 629-631 (1988).
DiMichele Lisa
Douglas Alan W.
King Steven A.
Verhoeven Thomas R.
Camara Valerie J.
Daniel Mark R.
Merck & Co. , Inc.
Springer David B.
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