US4010181A
Expired / Lapsed
US
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Process for the asymmetric hydrogenation of a substituted acrylic acid or ester thereof
Assignee: Rhone Poulenc SA
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Filing: 1975-06-25
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Granted: 1977-03-01
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Expires: 1995-06-25
Abstract
Abstract Optically active diphosphines of the formula, <IMAGE> in which the phosphinomethyl groups are trans to each other, form rhodium complexes useful as catalysts in hydrogenating substituted acrylic acids and their esters to optically active propionic acid derivatives.
Inventors
- 👤 Paul Aviron-Violet
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 22:37
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; B; B01; B01J; B01J31/00; B01J31/16; B01J31/24; B01J31/2404; B01J31/2409; B01J31/2414; B01J31/2442; B01J31/2447; B01J31/2452; B01J31/2457; C07F15/00; C07F15/0006; C07F15/0073; C07F15/008; C07F9/28; C07F9/50; C07F9/5027; B01J2231/00; B01J2231/60; B01J2231/64; B01J2231/641; B01J2231/645; B01J2531/00; B01J2531/80; B01J2531/82; B01J2531/822
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
145 words
A process for the asymmetric hydrogenation of a substituted acrylic acid or ester thereof, which comprises hydrogenating a mixture of the said acid or ester and a rhodium complex in which the rhodium is bound to halogen and a diphosphine of the formula: ##STR14##in which the phosphinomethyl groups are in the trans-position relative to one another, and the radicals R 1 , R 2 , R' 1 and R' 2 , which may be identical or different, each represent straight or branched alkyl of 1 to 8 carbon atoms, cycloalkyl of 5 or 6 ring carbon atoms, or aryl consisting of one or more benzene rings which are bonded to one another by a valency bond or which form with one another an ortho- or peri-condensed system, the said aryl being unsubstituted or substituted by straight or branched alkyl of 1 to 4 carbon atoms.
Claim 2
Dependent Claim
145 words
A process for the asymmetric hydrogenation of a substituted acrylic acid or ester thereof, which comprises hydrogenating a mixture of the said acid or ester and a rhodium complex in which the rhodium is bound to halogen and a diphosphine of the formula: ##STR14##in which the phosphinomethyl groups are in the trans-position relative to one another, and the radicals R 1 , R 2 , R' 1 and R' 2 , which may be identical or different, each represent straight or branched alkyl of 1 to 8 carbon atoms, cycloalkyl of 5 or 6 ring carbon atoms, or aryl consisting of one or more benzene rings which are bonded to one another by a valency bond or which form with one another an ortho- or peri-condensed system, the said aryl being unsubstituted or substituted by straight or branched alkyl of 1 to 4 carbon atoms.
Claim 3
Dependent Claim
104 words
Process according to claim 1 in which the substituted acrylic acid or ester thereof which is hydrogenated is a derivative of acrylic acid or an ester thereof in which one of the hydrogen atoms carried by the ethylenic carbon atoms is replaced by a primary or secondary amino or acylamino group and a second hydrogen atom carried by the ethylenic carbon atoms may be replaced by straight or branched alkyl, cycloalkyl, an unsubstituted or substituted aromatic hydrocarbon group, or a heterocyclic group containing one or more oxygen, sulphur, or nitrogen atoms, and no other hydrogen atoms carried by the ethylenic carbon atoms are replaced.
Claim 4
Dependent Claim
70 words
Process according to claim 2 in which the compound hydrogenated has the formula: ##STR15##where R 1 is alkyl of 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, phenyl, phenyl substituted in the 3- and/or 4- positions by hydroxy, methoxy, ethoxy, or methylenedioxy, naphthyl, or 3-indolyl, R 2 is hydrogen, alkyl of 1 to 4 carbon atoms, or phenyl, and R 3 is hydrogen or alkyl of 1 to 4 carbon atoms.
References Cited (Backward Citations)
US3798241A
Cited
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