Title:
CATALYST CAPABLE OF ALLOWING STRECKER REACTION TO PROCEED STEREOSELECTIVELY AND METHOD FOR STEREOSELECTIVELY PRODUCING α-AMINONITRILE DERIVATIVE USING THE SAME
Document Type and Number:
WIPO Patent Application WO/2007/074553
Kind Code:
A1
Abstract:
According to the invention, a catalyst for a strecker reaction comprising a quaternary
ammonium salt and a method for stereoselectively producing an α-aminonitrile
derivative using the same are provided. By using the α-aminonitrile derivative
obtained by the invention, an optically active α-amino acid and a derivative
thereof, which were difficult to produce by a conventional alkylation reaction
can be easily produced.
Inventors:
MARUOKA KEIJI (JP)
OOI TAKASHI (JP)
OOI TAKASHI (JP)
Application Number:
PCT/JP2006/314023
Publication Date:
July 05, 2007
Filing Date:
July 07, 2006
Export Citation:
Assignee:
NAGASE & CO LTD (JP)
UNIV KYOTO (JP)
MARUOKA KEIJI (JP)
OOI TAKASHI (JP)
UNIV KYOTO (JP)
MARUOKA KEIJI (JP)
OOI TAKASHI (JP)
International Classes:
B01J31/02; C07C303/36; C07C303/40; C07C311/19; C07D223/14; C07B53/00; C07B61/00
Domestic Patent References:
| WO2005073196A1 | 2005-08-11 |
Foreign References:
| JP2002326992A | 2002-11-15 | |||
| JP2001089434A | 2001-04-03 | |||
| JP2004510298A | 2004-04-02 | |||
| US2619484A | 1952-11-25 |
Other References:
STARA I.G. ET AL.: "Optically Pure (S)- and (R)-4,5-Dihydro-3H-4-Methyldinaphth[2,1-c;1',2'-e]Azepines. Application to the Synthesis of New Bidentate Ligands with Axial Asymmetry", TETRAHEDRON: ASYMMETRY, vol. 3, no. 11, 1992, pages 1365 - 1368, XP002987956
COTTINEAU F. ET AL.: "Reductive Cleavage of Axially Disymmetric Tertiary Amines and Quaternary Ammonium Salts by Lithium Aluminum Hydride. Synthesis of New 1,1'-Binaphthyl Substituted Amines", TETRAHEDRON LETTERS, vol. 26, no. 4, 1985, pages 421 - 424, XP002278770
ABOUL-ENEIN H.Y. ET AL.: "Synthesis and Biological Activity of Dibenz[c,e]Azepines", DRUG DESIGN AND DELIVERY, vol. 4, no. 1, 1989, pages 27 - 33, XP002987985
TAYLOR E.C. ET AL.: "Thallium in Organic synthesis. 59. Alkaloid Synthesis via Intramolecular Nonphenolic Oxidative Coupling. Preparation of (plus or minus)-Ocoteine, (plus or minus)-Acetoxyocoxylonine, (plus or minus)-3-Methoxy-N-acetylnornantenine, (plus or minus)......", J. AM. CHEM. SOC., vol. 102, no. 21, 1980, pages 6513 - 6519, XP003002928
RUFFOLO R.R. ET AL.: "Kinetics of Accumulation, Efflux and the Pharmacological Effects of Tritiated Dihydroazapetine on the Rabbit Aorta", THE JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 202, no. 2, 1977, pages 278 - 286, XP003002929
AMES D.E. ET AL.: "Synthesis of 4,5-Bridged Carbazoles", JOURNAL OF THE CHEMICAL SOCIETY PERKIN TRANSACTIONS I, no. 22, 1973, pages 2818 - 2824, XP003002930
FRASER R.R. ET AL.: "Dihedral Angular Dependence of H-N-C-H Coupling Constants. Protonated Amines in Trifluoroacetic Acid", CANADIAN JOURNAL OF CHEMISTRY, vol. 51, no. 15, 1973, pages 2433 - 2437, XP003002931
BONNER R.B. ET AL.: "Phosphorescence of Bridged Biphenyls in Fluid Solution", J. AM. CHEM. SOC., vol. 94, no. 3, 1972, pages 988 - 989, XP003002932
AHMED S.R. ET AL.: "Steric Effects of 2:2'-Bridged Diphenyls with a Heterocyclic Bridging Ring. Part I. Optically Active Dihydrodibenzazepines", JOURNAL OF THE CHEMICAL SOCIETY, 1958, pages 3043 - 3047, XP003002933
RANDALL L.O. ET AL.: "The Adrenergic Blocking Action of Some Dibenzazepine Derivatives", THE JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 103, 1951, pages 10 - 23, XP003002934
COTTINEAU F. ET AL.: "Reductive Cleavage of Axially Disymmetric Tertiary Amines and Quaternary Ammonium Salts by Lithium Aluminum Hydride. Synthesis of New 1,1'-Binaphthyl Substituted Amines", TETRAHEDRON LETTERS, vol. 26, no. 4, 1985, pages 421 - 424, XP002278770
ABOUL-ENEIN H.Y. ET AL.: "Synthesis and Biological Activity of Dibenz[c,e]Azepines", DRUG DESIGN AND DELIVERY, vol. 4, no. 1, 1989, pages 27 - 33, XP002987985
TAYLOR E.C. ET AL.: "Thallium in Organic synthesis. 59. Alkaloid Synthesis via Intramolecular Nonphenolic Oxidative Coupling. Preparation of (plus or minus)-Ocoteine, (plus or minus)-Acetoxyocoxylonine, (plus or minus)-3-Methoxy-N-acetylnornantenine, (plus or minus)......", J. AM. CHEM. SOC., vol. 102, no. 21, 1980, pages 6513 - 6519, XP003002928
RUFFOLO R.R. ET AL.: "Kinetics of Accumulation, Efflux and the Pharmacological Effects of Tritiated Dihydroazapetine on the Rabbit Aorta", THE JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 202, no. 2, 1977, pages 278 - 286, XP003002929
AMES D.E. ET AL.: "Synthesis of 4,5-Bridged Carbazoles", JOURNAL OF THE CHEMICAL SOCIETY PERKIN TRANSACTIONS I, no. 22, 1973, pages 2818 - 2824, XP003002930
FRASER R.R. ET AL.: "Dihedral Angular Dependence of H-N-C-H Coupling Constants. Protonated Amines in Trifluoroacetic Acid", CANADIAN JOURNAL OF CHEMISTRY, vol. 51, no. 15, 1973, pages 2433 - 2437, XP003002931
BONNER R.B. ET AL.: "Phosphorescence of Bridged Biphenyls in Fluid Solution", J. AM. CHEM. SOC., vol. 94, no. 3, 1972, pages 988 - 989, XP003002932
AHMED S.R. ET AL.: "Steric Effects of 2:2'-Bridged Diphenyls with a Heterocyclic Bridging Ring. Part I. Optically Active Dihydrodibenzazepines", JOURNAL OF THE CHEMICAL SOCIETY, 1958, pages 3043 - 3047, XP003002933
RANDALL L.O. ET AL.: "The Adrenergic Blocking Action of Some Dibenzazepine Derivatives", THE JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 103, 1951, pages 10 - 23, XP003002934
Attorney, Agent or Firm:
NANJO, Hiromichi (Okina Bldg. 2-9, Nishitenma 3-chome, Kita-k, Osaka-shi Osaka 47, JP)
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