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EP0115860A2
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Optically active 4-hydroxy-2-cyclopentenones, and their production
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1984-02-02
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Granted: —
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Expires: 2004-02-02
Abstract
Abstract A process for preparing an optically active 4-hydroxy-2- cylopentenone of the formula: wnerem R 1 is a nyarogen atom or a methyl group, R 2 is an alkyl group, an alkenyl group or an alkynyl group and the asterisk ( * ) indicates an asymmetric configuration, which comprises subjecting an optically active 4-cylopentenone-alcohol of the formula: wherein R 1 and R 2 are each as defined above, the asterisk ( * ) indicates an asymmetric configuration and the substituents R 1 and R 2 take a cis-configuration to rearrangement while maintainig the original steric configuration.
Inventors
- 👤 Masayoshi Minai
- 👤 Tadashi Katsura
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 16:41
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/67; C07C49/00; C07C49/587; C07C49/703; C07C49/707; C07C49/743; C12; C12P; C12P41/00; C12P41/003; C12P41/004; C12P7/00; C12P7/24; C12P7/26; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/874
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
96 words
A process for preparing an optically active 4-hydroxy-2-cyclopentenone of the formula: wherein R 1 is a hydrogen atom or a methyl group, R 2 is an alkyl group, an alkenyl group or an alkynyl group and the asterisk ( * ) indicates an asymmetric configuration, which comprises subjecting an optically active 4-cyclopentenone-alcohol of the formula: wherein R 1 and R 2 are each as defined above, the asterisk ( * ) indicates an asymmetric configuration and the substi- , tuents R 1 and R 2 take a cis-configuration to rearrangement while maintaining the original steric configuration.
Claim 2
Dependent Claim
96 words
A process for preparing an optically active 4-hydroxy-2-cyclopentenone of the formula: wherein R 1 is a hydrogen atom or a methyl group, R 2 is an alkyl group, an alkenyl group or an alkynyl group and the asterisk ( * ) indicates an asymmetric configuration, which comprises subjecting an optically active 4-cyclopentenone-alcohol of the formula: wherein R 1 and R 2 are each as defined above, the asterisk ( * ) indicates an asymmetric configuration and the substi- , tuents R 1 and R 2 take a cis-configuration to rearrangement while maintaining the original steric configuration.
Claim 3
Dependent Claim
62 words
The process according to claim 1, wherein the optically active 4-cyclopentenone-alcohol is the one prepared by subjecting a racemic or optically active 4-cyclopentenone ester of the formula: wherein R 1 and R 2 are each as defined above, R is an acyloxy group and the substituents R 1 and R 2 take a cis-configuration to asymmetric hydrolysis with an enzyme or microorganism.
Claim 4
Dependent Claim
54 words
The process according to claim 2, wherein the 4-cyclopentenone ester is the one prepared by reacting a racemic 4-cyclopentenone-alcohol of the formula: wherein R 1 and R 2 are each as defined above and the substituents R 1 and R 2 take a cis-configuration with an aliphatic . carboxylic acid or its reactive derivative.
Claim 5
Dependent Claim
82 words
The process according to claim 1, wherein the optically active 4-cyclopentenone-alcohol is the one prepared by subjecting a racemic 4-cyclopentenone ester of the formula: wherein R 1 and R 2 are each as defined above, R is an acyloxy group and the substituents R 1 and R 2 take a cis-configuration to asymmetric hydrolysis with an enzyme or microorganism, separating the unhydrolyzed optical isomer of the 4-cyclopentenone ester and subjecting the recovered unhydrolyzed optical isomer to hydrolysis with an enzyme or microorganism.
Claim 6
Dependent Claim
16 words
The process according to any one of claims 1 to 4, wherein R 1 is methyl.
Claim 7
Dependent Claim
24 words
The process according to claim 5, wherein the optically active 4-cyclopentenone-alcohol is the ℓ-form and the optically active 4-hydroxy-2 - cyclopentenone is the S(+)-form.
Claim 8
Dependent Claim
22 words
The process according to claim 5, wherein the optically active 4-cyclopentenone-alcohol is the d-form and the optically active 4-hydroxy-2-cyclopentenone is the R(-)-form.
Claim 9
Dependent Claim
30 words
The process according to claim 5, wherein the optically active 4-cyclopentenone ester is the d-form, the optically active 4-cyclopentenone-alcohol is the ℓ-form and the optically active 4-hydroxy-2-cyclopentenone is the S(+)-form.
Claim 10
Dependent Claim
30 words
The process according to claim 5, wherein the optically active 4-cyclopentenone ester is the ℓ-form, the optically active 4-cyclopentenone-alcohol is the d-form and the optically active 4-hydroxy-2-cyclopentenone is the R(-)-form.
Claim 11
Dependent Claim
16 words
The process according to any one of claims 1 to 4, wherein R 1 is hydrogen.
Claim 12
Dependent Claim
22 words
The process according to claim 10, wherein the optically active 4-cyclopentenone-alcohol is the ℓ-form and the optically active 4-hydroxy-2-cyclopentenone is the R(+)-form.
Claim 13
Dependent Claim
30 words
The process according to claim 10, wherein the optically active 4-cyclopentenone ester is the d-form,. the optically active 4-cyclopentenone-alcohol is the d-form and the optically active 4-hydroxy-2-cyclopentenone is the S(-)-form.
Claim 14
Dependent Claim
34 words
The process according to claim 1, wherein the rearrangement is carried out in the presence of a catalyst selected from the group consisting of organic tertiary amines, metal oxides, inorganic bases and basic buffers.
Claim 15
Dependent Claim
23 words
The process according to claim 13, wherein the catalyst is an organic tertiary amine chosen from triethylamine, N-methylmorpholine, N-methylpipieridine, N,N'-dimethylpiperazine, pyridine and lutidine.
Claim 16
Dependent Claim
19 words
The process according to claim 13, wherein the catalyst is a metal oxide chosen from alumina and silica gel.
Claim 17
Dependent Claim
32 words
. The process according to claim 13, wherein the catalyst is an inorganic base chosen from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate and potassium monohydrogen phosphate.
Claim 18
Dependent Claim
22 words
The process according to claim 13, wherein the catalyst is a basic buffer chosen from carbonate buffers, phosphate buffers and borate buffers.
Claim 19
Dependent Claim
32 words
The process according to claim 13, wherein the catalyst is used in an amount of 0.05 to 60 parts by , weight to one part by weight of the optically active 4-cyclopentenone-alcohol.
Claim 20
Dependent Claim
19 words
The process according to claim 1, wherein the rearrangement is carried out at a temperature of -20 to 130°C.
Claim 21
Dependent Claim
69 words
The process according to claim 2 or 4, wherein the enzyme is the one obtained from the microorganism belonging to any one of Rhodotorula, Trichoderma, Candida, Pseudomonas, Hansenula, Bacillus, Achromobacter, Nocardia, Chromobacterium, Flavobacterium, Rhizopus, Mucor, Aspergillus, Alcaligenes, T orulopsis, Corynebacterium, Endomyces, Saccharomyces, Arthrobacter, Metshnikowia, Pleurotus, Streptomyces, Proteus, Gliocladium, Acetobacter, Helminthosporium, Brevibacterium, Escherichia, Citrobacter, Micrococcus, Pediococcus, Klebsiella, Absidia, Geotrichem, Streptomyces, Lactobacillus, Cryptococcus, Pichia, Aureobasidium, Actimomucor, Enterobacter, Microbacterium, Penicillium and Schizophyllum.
Claim 22
Dependent Claim
19 words
The process according to claim 20, wherein the enzyme is the one obtained from the microorganism belonging to Pseudomonas.
Claim 23
Dependent Claim
17 words
The process according to claim 21, wherein the microorganism is Pseudomonas fragi, Pseudomonas fluorescens or Pseudomonas aeruginosa.
Claim 24
Dependent Claim
31 words
The process according to claim 20, wherein the enzyme is the one obtained from the microorganism belonging to Trichoderma, Candida, Hansenula, Bacillus, Achromobacter, Nocardia, Chromobacterium, Flavobacterium, Torulopsis, Metshnikowia, Pleurotus or Schizophyllum.
Claim 25
Dependent Claim
41 words
The process according to claim 23, wherein the microorganism is Candida cylindracea, Hansenula anomala var. ciferrii, Metshnikowia pulcherrima, Pleurotus octreatus, Schizophyllum commune, Candida krusei, Bacillus subtilis, Achromobacter parvulus, Flavobacterium lutesens, Chromobacterium iodinum, Nocardia uniformis subptsuyama- nenus, Torulopsis ernobii or Trichoderma longibrachiatum.
Claim 26
Dependent Claim
64 words
The process according to claim 2 or 4, wherein the microorganism is the one belonging to any one of Rhodotorula, Trichoderma, Candida, Pseudomonas, Hansenula, Bacillus, Achromobacter, Nocardia, Chromobacterium, Flavobacterium, Rhizopus, Mucor, Aspergillus, Alcaligenes, Torulopsis, Corynebacterium, Endomyces, Saccharomyces, Arthrobacter, Metshnikowia, Pleurotus, Streptomyces, Proteus, Gliocladium, Acetobacter, Helminthosporium, Brevibacterium, Escherichia, Citrobacter, Micrococcus, Pediococcus, Klebsiella, Absidia, Geotrichem, Streptomyces, Lactobacillus, Cryptococcus, Pichia, Aureobasidium, Schizophyllum, Actimomucor, Enterobacter, Microbacterium and Penicillium.
Claim 27
Dependent Claim
15 words
The process according to claim 25, wherein the microorganism is the one belonging to Pseudomonas.
Claim 28
Dependent Claim
17 words
The process according to claim 26, wherein the microorganism is Pseudomonas fragi, Pseudomonas fluorescens or Pseudomonas aeruginosa.
Claim 29
Dependent Claim
27 words
The process according to claim 25, wherein the microorganism is the one belonging to Trichoderma, Candida, Hansenula, Bacillus, Achromobacter, Nocardia, Chromobacter, Flavobacterium, Torulopsis, Metshnikowia, Pleurotus or Schizophyllum.
Claim 30
Dependent Claim
41 words
The process according to claim 28, wherein the microorganism is Candida cylindracea, Hansenula anomala var. ciferrii, Metshnikowia pulcherrima, Pleurotus octreatus, Schizophyllum commune, Candida krusei, Bacillus subtilis, Achromobacter parvulus, Flavobacterium lutesens, Chromobacterium iodinum, Nocardia uniformis subptsuyama- nenus, Torulopsis ernobii or Trichoderma longibrachiatum.
Claim 31
Dependent Claim
50 words
An optically active 4-cyclopentenone of the formula: wherein R 1 is a hydrogen atom, R 2 is a lower alkyl group, a lower alkenyl group or a lower alkynyl group, R is a hydroxyl group or an acyloxy group and the substituents R 1 and R 2 take a cis-configuration.
Claim 32
Dependent Claim
50 words
An optically active 4-cyclopentenone of the formula: wherein R 1 is a hydrogen atom, R 2 is a lower alkyl group, a lower alkenyl group or a lower alkynyl group, R is a hydroxyl group or an acyloxy group and the substituents R 1 and R 2 take a cis-configuration.
Claim 33
Dependent Claim
12 words
The optically active 4-cyclopentenone according to claim 30, wherein R is hydroxyl.
Claim 34
Dependent Claim
12 words
The optically active 4-cyclopentenone according to claim 30, wherein R is acetoxy.
References Cited (Backward Citations)
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