US4124533A
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US
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Metal coordination complexes containing optically active phosphine or arsine ligands
Assignee: Monsanto Co
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Filing: 1975-03-17
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Granted: 1978-11-07
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Expires: 1995-03-17
Abstract
Abstract Process for the homogeneous catalytic hydrogenation of β-substituted-α-acylamido-acrylic acids which yields, after hydrogenation, an optically active mixture. The process comprises the hydrogenation of β-substituted-α-acylamido-acrylic acids in the presence of an optically active coordinated metal complex hydrogenation catalyst, in which the metal is selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum. This process is a generalized process for any asymmetric hydrogenation of β-substituted-α-acylamido-acrylic acids in which one α-amino acid enantiomorph is the desired end-product. It is especially useful for the preparation of α-amino acids found in nature which possess optical activity and which have a hydrogen attached to the asymmetric center. This invention also relates to new optically active coordinated metal complex hydrogenation catalysts.
Inventors
- 👤 William S. Knowles
- 👤 Milton J. Sabacky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 13:51
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/50; C07F9/53; B; B01; B01J; B01J31/00; B01J31/16; B01J31/22; B01J31/2282; B01J31/2291; B01J31/24; B01J31/2404; C07F9/30; C07F9/32; C07F9/34; C07F9/38; C07F9/40; B01J2231/00; B01J2231/60; B01J2231/64; B01J2231/641; B01J2231/645; B01J2531/00; B01J2531/80; B01J2531/82; B01J2531/821; B01J2531/822; B01J2531/824; B01J2531/825; B01J2531/827; B01J2531/828
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
61 words
An optically active metal coordination complex of the formula M 1 X n L 3 wherein M 1 is rhodium, X is selected from the group consisting of hydrogen, chlorine, fluorine, bromine and iodine, n is one of the integers one or three; each L is a phosphine or arsine ligand, provided that at least one L group is optically active.
Claim 2
Dependent Claim
61 words
An optically active metal coordination complex of the formula M 1 X n L 3 wherein M 1 is rhodium, X is selected from the group consisting of hydrogen, chlorine, fluorine, bromine and iodine, n is one of the integers one or three; each L is a phosphine or arsine ligand, provided that at least one L group is optically active.
Claim 3
Dependent Claim
13 words
A compound in accordance with claim 1 in which L is a phosphine.
Claim 4
Dependent Claim
15 words
A compound in accordance with claim 2 in which the phosphine contains an o-anisyl group.
Claim 5
Dependent Claim
15 words
A compound in accordance with claim 3 in which the phosphine contains a methyl group.
Claim 6
Dependent Claim
13 words
A compound in accordance with claim 4 in which the phosphine is methylphenyl-o-anisylphosphine.
Claim 7
Dependent Claim
13 words
A compound in accordance with claim 4 in which the phosphine is methylcyclohexyl-o-anisylphosphine.
Claim 8
Dependent Claim
43 words
A catalyst comprising a solution of a metal selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum and at least one equivalent of a phosphine or arsine ligand per mole of metal, provided that the ligand is optically active.
Claim 9
Dependent Claim
43 words
A catalyst comprising a solution of a metal selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum and at least one equivalent of a phosphine or arsine ligand per mole of metal, provided that the ligand is optically active.
Claim 10
Dependent Claim
12 words
A catalyst according to claim 7 in which the metal is rhodium.
Claim 11
Dependent Claim
49 words
A catalyst according to claim 8 in which the phosphine or arsine has at least one phenyl group that has a substituent in the ortho position selected from the group consisting of hydroxy; alkoxy having at least one carbon atom and a maximum of twelve carbon atoms; and aryloxy.
Claim 12
Dependent Claim
12 words
A catalyst according to claim 9 in which the phosphine is methylphenyl-o-anisylphosphine.
Claim 13
Dependent Claim
12 words
A catalyst according to claim 9 in which the phosphine is methylcyclohexyl-o-anisylphoshine.
Claim 14
Dependent Claim
26 words
A solid, cationic coordination rhodium complex containing 2 equivalents of an optically active phosphine or arsine ligand per mole of rhodium and a chelating bis olefin.
Claim 15
Dependent Claim
26 words
A solid, cationic coordination rhodium complex containing 2 equivalents of an optically active phosphine or arsine ligand per mole of rhodium and a chelating bis olefin.
Claim 16
Dependent Claim
10 words
A compound of claim 12 which is cyclooctadiene-1,5-bis(methylcyclohexyl-o-anisylphosphine) rhodium tetrafluoroborate.
Claim 17
Dependent Claim
10 words
A compound of claim 12 which is cyclooctadiene-1,5-bis(methylcyclohexyl-o-anisylphosphine) rhodium tetraphenylborate.
Claim 18
Dependent Claim
10 words
A compound of claim 12 which is bicyclo-2.2.1-hepta-2,5-diene-bis(methylcyclohexyl-o-anisylphosphine) rhodium tetrafluoroborate.
References Cited (Backward Citations)
US3133943A
Cited
US3489786A
Cited
US3759838A
Cited
US3480659A
Cited
US3511880A
Cited
US3652614A
Cited
US3849480A
Cited
US4008281A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-11-06 | 1982-05-08 | 1982-11-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-06 | 1986-05-08 | 1986-11-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-06 | 1990-05-08 | 1990-11-07 | $7700.00 | Window Closed / Lapsed |