Title:
PROCESSES FOR THE PREPARATION OF OPTICALLY ACTIVE KETONES
Document Type and Number:
WIPO Patent Application WO/1998/000382
Kind Code:
A1
Abstract:
Processes for preparing optically active esters by reacting racemic alcohols with optically active amino acid derivatives or optically active tartaric acid derivatives; processes for preparing optically active alcohols by hydrolyzing the esters; processes for preparing ketones by oxidizing the alcohols; processes for storing the optically active ketones stably; and novel optically active amino acid esters and optically active tartaric acid esters which are useful as the intermediates for the preparation of drugs or agricultural chemicals.
Inventors:
SATO HARUYO (JP)
NAKAI SAKIE (JP)
FUNABASHI KEIKO (JP)
IWATA SHIHO (JP)
NAKAI SAKIE (JP)
FUNABASHI KEIKO (JP)
IWATA SHIHO (JP)
Application Number:
PCT/JP1997/002294
Publication Date:
January 08, 1998
Filing Date:
July 02, 1997
Export Citation:
Assignee:
TORAY INDUSTRIES (JP)
SATO HARUYO (JP)
NAKAI SAKIE (JP)
FUNABASHI KEIKO (JP)
IWATA SHIHO (JP)
SATO HARUYO (JP)
NAKAI SAKIE (JP)
FUNABASHI KEIKO (JP)
IWATA SHIHO (JP)
International Classes:
C07C27/02; C07C29/09; C07C29/143; C07C45/30; C07C45/85; C07C69/675; C07C69/70; C07C231/18; C07C233/45; C07C233/83; C07C233/86; (IPC1-7): C07C31/00; C07C27/02; C07C29/09; C07C233/83; C07C231/18; C07C67/08; C07C69/708; C07C271/22; C07C49/385; C07C45/30; C07C45/78; C07C49/04; C07C49/517; C07C227/34; C07C231/20; C07C311/00; C07C303/44; C07D307/60; C07D209/42; C07D209/48; C07B57/00
Foreign References:
| JPH04273835A | 1992-09-30 | |||
| JPH05279325A | 1993-10-26 | |||
| JPH05279326A | 1993-10-26 | |||
| JPS5756750A | 1982-04-05 | |||
| JPS5136439A | 1976-03-27 | |||
| US5721803A | 1998-02-24 | |||
| EP0199257A2 | 1986-10-29 | |||
| DE2854932A1 | 1979-07-05 | |||
| GB2283971A | 1995-05-24 | |||
| JPH01199956A | 1989-08-11 | |||
| JPH0459742A | 1992-02-26 | |||
| JPH04211629A | 1992-08-03 | |||
| JPS6388148A | 1988-04-19 | |||
| JPS636053B2 | 1988-02-08 | |||
| JPH06135881A | 1994-05-17 | |||
| JPH0651654B2 | 1994-07-06 | |||
| JPH09110776A | 1997-04-28 | |||
| JPH06507940A | 1994-09-08 | |||
| JPH01100142A | 1989-04-18 | |||
| JPH08176055A | 1996-07-09 |
Other References:
J. CHEM. SOC., PERKIN TRANS. 1, 21 December 1996, No. 24, ALLER ENRIQUE et al., "N-H Insertion Reactions of Rhodium Carbenoids, Part 1. Preparation of alpha-Amino Acid and alpha-Aminophosphonic Acid Derivatives", p. 2879-2884.
BIOORGANIC & MEDICINAL CHEM. LETT., (1994), Vol. 4, No. 8, KIM L. DUEHOLM et al., "Peptide Nucleic Acid with a Chiral Backbone Based on Alanine", p. 1077-1080.
J. MED. CHEM., (1990), Vol. 33, No. 3, JANUSZ J.M. et al., "High Potency Dipeptide Sweetners. 1. L-Aspartyl-D-Phenylglycine Esters", p. 1052-1061.
TETRAHEDRON, (1988), Vol. 44, No. 17, CASTELHANO ARLINDO L. et al., "Synthesis of .alpha.-Amino Acids with .beta., gamma.-Unsaturated Side Chains", p. 5451-5466.
J. PRAKT. CHEM./ CHEM.-ZTG., (1994), Vol. 336, No. 4, EBBELING SABINE C., "Elucidation of the Stereochemistry of the .alpha.-Amido Alkylation Products Resulting from the Interaction of Allyltrimethylsilane with Electrophilic Glycine Menthyl Ester Derivatives", p. 33-332.
J. ORG. CHEM., (1982), Vol. 47, No. 20, BARTLETT PAUL A., "Ester-Enolate Claisen Rearrangement of .alpha.-Amino Acid Derivatives", p. 3933-3941.
J. ORG. CHEM., (1980), Vol. 45, No. 17, GLUCHOWSKI CHARLES, "Preparation of .beta.-Lactams by the Condensation of Lithium Ester Enolates with Aryl Aldimines", p. 3413-3416.
SYNTHESIS, 31 December 1996, No. 12, KAZMAIER ULI, "Synthesis of Allenic Amino Acids via Chelate-Controlled Ester Enolate Claisen Rearrangement", p. 1489-1493.
TETRAHEDRON: ASSYMMETRY, (1993), Vol. 4, No. 7, TH. KUNSTLER et al., "Synthesis of Optically Pure Alkynols", p. 1645-1650.
AUST. J. CHEM., (1987), Vol. 40, K.H. BELL, "Relative Stereoselectivity of the Reactions of (2R,3R)- and (2R,2S)-2,3-Dibenzoyloxysuccinic Anhydrides with Chiral Amines and Alcohols", p. 399-404.
AFINIDAD, (1975), Vol. 32, No. 331, S. JULIA, "IV. Resolucion de Alcoholes Racemicos, via Separation de Esters Diasteoisomeros por CGL. Influencia de Agente Resolvente en la Saparacion", p. 971-975.
See also references of EP 0924180A4
BIOORGANIC & MEDICINAL CHEM. LETT., (1994), Vol. 4, No. 8, KIM L. DUEHOLM et al., "Peptide Nucleic Acid with a Chiral Backbone Based on Alanine", p. 1077-1080.
J. MED. CHEM., (1990), Vol. 33, No. 3, JANUSZ J.M. et al., "High Potency Dipeptide Sweetners. 1. L-Aspartyl-D-Phenylglycine Esters", p. 1052-1061.
TETRAHEDRON, (1988), Vol. 44, No. 17, CASTELHANO ARLINDO L. et al., "Synthesis of .alpha.-Amino Acids with .beta., gamma.-Unsaturated Side Chains", p. 5451-5466.
J. PRAKT. CHEM./ CHEM.-ZTG., (1994), Vol. 336, No. 4, EBBELING SABINE C., "Elucidation of the Stereochemistry of the .alpha.-Amido Alkylation Products Resulting from the Interaction of Allyltrimethylsilane with Electrophilic Glycine Menthyl Ester Derivatives", p. 33-332.
J. ORG. CHEM., (1982), Vol. 47, No. 20, BARTLETT PAUL A., "Ester-Enolate Claisen Rearrangement of .alpha.-Amino Acid Derivatives", p. 3933-3941.
J. ORG. CHEM., (1980), Vol. 45, No. 17, GLUCHOWSKI CHARLES, "Preparation of .beta.-Lactams by the Condensation of Lithium Ester Enolates with Aryl Aldimines", p. 3413-3416.
SYNTHESIS, 31 December 1996, No. 12, KAZMAIER ULI, "Synthesis of Allenic Amino Acids via Chelate-Controlled Ester Enolate Claisen Rearrangement", p. 1489-1493.
TETRAHEDRON: ASSYMMETRY, (1993), Vol. 4, No. 7, TH. KUNSTLER et al., "Synthesis of Optically Pure Alkynols", p. 1645-1650.
AUST. J. CHEM., (1987), Vol. 40, K.H. BELL, "Relative Stereoselectivity of the Reactions of (2R,3R)- and (2R,2S)-2,3-Dibenzoyloxysuccinic Anhydrides with Chiral Amines and Alcohols", p. 399-404.
AFINIDAD, (1975), Vol. 32, No. 331, S. JULIA, "IV. Resolucion de Alcoholes Racemicos, via Separation de Esters Diasteoisomeros por CGL. Influencia de Agente Resolvente en la Saparacion", p. 971-975.
See also references of EP 0924180A4
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