US4142992A
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Asymmetric catalysis
Assignee: Monsanto Co
•
Filing: 1976-09-16
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Granted: 1979-03-06
•
Expires: 1996-09-16
Abstract
Abstract New optically active bis phosphine compounds which are useful in optically active catalysts. Such catalysts are particularly useful in catalytic asymmetric hydrogenation.
Inventors
- 👤 William S. Knowles
- 👤 Milton J. Sabacky
- 👤 Billy D. Vineyard
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 20:08
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/16; B01J31/24; B01J31/2404; B01J31/2409; B01J31/2414; C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/50; C07F9/5027; B01J2231/00; B01J2231/60; B01J2231/64; B01J2231/641; B01J2231/645; B01J2531/00; B01J2531/80; B01J2531/82; B01J2531/821; B01J2531/822; B01J2531/827
Claims Analysis
Total Claims: 50
Claim 1
Independent Claim
100 words
A coordinated complex catalyst comprising a transition metal selected from the group consisting of rhodium, iridium and ruthenium in combination with from about 0.5 to about 2.0 moles per mole of metal of an optically active bis phosphine ligand represented by the structural formula ##STR10## wherein A and B each independently represent substituted and unsubstituted alkyl of from 1 to 12 carbon atoms, substituted and unsubstituted cycloalkyl having from 4 to 7 carbon atoms, substituted and unsubstituted aryl; provided that such substiuents provide no significant interference with the steric requirements around the phosphorus atom and A and B are different.
Claim 2
Dependent Claim
100 words
A coordinated complex catalyst comprising a transition metal selected from the group consisting of rhodium, iridium and ruthenium in combination with from about 0.5 to about 2.0 moles per mole of metal of an optically active bis phosphine ligand represented by the structural formula ##STR10## wherein A and B each independently represent substituted and unsubstituted alkyl of from 1 to 12 carbon atoms, substituted and unsubstituted cycloalkyl having from 4 to 7 carbon atoms, substituted and unsubstituted aryl; provided that such substiuents provide no significant interference with the steric requirements around the phosphorus atom and A and B are different.
Claim 3
Dependent Claim
12 words
A catalyst according to claim 1 wherein the transition metal is rhodium.
Claim 4
Dependent Claim
14 words
A catalyst according to claim 1 wherein A and B are dissimilar aryl groups.
Claim 5
Dependent Claim
12 words
A catalyst according to claim 3 wherein the transition metal is rhodium.
Claim 6
Dependent Claim
19 words
A catalyst according to claim 3 wherein one such aryl group has an alkoxy substituent at the ortho position.
Claim 7
Dependent Claim
12 words
A catalyst according to claim 5 wherein the transition metal is rhodium.
Claim 8
Dependent Claim
63 words
A catalyst according to claim 1 wherein the bis phosphine ligand is represented by the structural formula ##STR11## wherein X represents substituted and unsubstituted phenyl, Y represents substituted and unsubstituted 2-alkoxyphenyl wherein the alkoxy has from 1 to 6 carbon atoms; provided that such substituents provide no significant interference with the steric requirements around the phosphorus atom and X and Y are different.
Claim 9
Dependent Claim
12 words
A catalyst according to claim 7 wherein the transition metal is rhodium.
Claim 10
Dependent Claim
65 words
A catalyst according to claim 1 wherein the bis phosphine ligand is represented by the structural formula ##STR12## R 1 and R 2 each independently represent hydrogen, halogen, alkyl having from 1 to 6 carbon atoms and alkoxy having from 1 to 6 carbon atoms, and R 3 represents normal alkyl having from 1 to 6 carbon atoms; provided that M and N are different.
Claim 11
Dependent Claim
12 words
A catalyst according to claim 9 wherein the transition metal is rhodium.
Claim 12
Dependent Claim
36 words
A coordinated complex catalyst comprising a transition metal selected from the group consisting of rhodium, iridium and ruthenium in combination with from about 0.5 to 2.0 moles per mole of metal of optically active 1,2-bis(o-anisylphenylphosphino) ethane.
Claim 13
Dependent Claim
36 words
A coordinated complex catalyst comprising a transition metal selected from the group consisting of rhodium, iridium and ruthenium in combination with from about 0.5 to 2.0 moles per mole of metal of optically active 1,2-bis(o-anisylphenylphosphino) ethane.
Claim 14
Dependent Claim
12 words
A catalyst according to claim 11 wherein the transition metal is rhodium.
Claim 15
Dependent Claim
22 words
A catalyst according to claim 11 wherein optically active bis(o-anisylphenylphosphino) ethane is present in about 1.0 mole per mole of transition metal.
Claim 16
Dependent Claim
12 words
A catalyst according to claim 13 wherein the transition metal is rhodium.
Claim 17
Dependent Claim
35 words
A catalyst according to claim 1 which is a solid, cationic coordination metal complex containing one mole of the optically active bis phosphine ligand per mole of metal, a chelating bis olefin and an anion.
Claim 18
Dependent Claim
12 words
A catalyst according to claim 15 wherein the transition metal is rhodium.
Claim 19
Dependent Claim
35 words
A catalyst according to claim 3 which is a solid, cationic coordination metal complex containing one mole of the optically active bis phosphine ligand per mole of metal, a chelating bis olefin and an anion.
Claim 20
Dependent Claim
12 words
A catalyst according to claim 17 wherein the transition metal is rhodium.
Claim 21
Dependent Claim
35 words
A catalyst according to claim 5 which is a solid, cationic coordination metal complex containing one mole of the optically active bis phosphine ligand per mole of metal, a chelating bis olefin and an anion.
Claim 22
Dependent Claim
12 words
A catalyst according to claim 19 wherein the transition metal is rhodium.
Claim 23
Dependent Claim
35 words
A catalyst according to claim 7 which is a solid, cationic coordination metal complex containing one mole of the optically active bis phosphine ligand per mole of metal, a chelating bis olefin and an anion.
Claim 24
Dependent Claim
12 words
A catalyst according to claim 21 wherein the transition metal is rhodium.
Claim 25
Dependent Claim
35 words
A catalyst according to claim 9 which is a solid, cationic coordination metal complex containing one mole of the optically active bis phosphine ligand per mole of metal, a chelating bis olefin and an anion.
Claim 26
Dependent Claim
12 words
A catalyst according to claim 23 wherein the transition metal is rhodium.
Claim 27
Dependent Claim
35 words
A catalyst according to claim 11 which is a solid, cationic coordination metal complex containing one mole of the optically active bis phosphine ligand per mole of metal, a chelating bis olefin and an anion.
Claim 28
Dependent Claim
12 words
A catalyst according to claim 25 wherein the transition metal is rhodium.
Claim 29
Dependent Claim
35 words
A catalyst according to claim 13 which is a solid, cationic coordination metal complex containing one mole of the optically active bis phosphine ligand per mole of metal, a chelating bis olefin and an anion.
Claim 30
Dependent Claim
12 words
A catalyst according to claim 27 wherein the transition metal is rhodium.
Claim 31
Dependent Claim
33 words
A catalyst according to claim 1 wherein the catalyst comprises a solution of a transition metal selected from the group consisting of rhodium, iridium and ruthenium and the optically active bis phosphine ligand.
Claim 32
Dependent Claim
12 words
A catalyst according to claim 29 wherein the transition metal is rhodium.
Claim 33
Dependent Claim
33 words
A catalyst according to claim 3 wherein the catalyst comprises a solution of a transition metal selected from the group consisting of rhodium, iridium and ruthenium and the optically active bis phosphine ligand.
Claim 34
Dependent Claim
12 words
A catalyst according to claim 31 wherein the transition metal is rhodium.
Claim 35
Dependent Claim
33 words
A catalyst according to claim 5 wherein the catalyst comprises a solution of a transition metal selected from the group consisting of rhodium, iridium and ruthenium and the optically active bis phosphine ligand.
Claim 36
Dependent Claim
12 words
A catalyst according to claim 33 wherein the transition metal is rhodium.
Claim 37
Dependent Claim
33 words
A catalyst according to claim 7 wherein the catalyst comprises a solution of a transition metal selected from the group consisting of rhodium, iridium and ruthenium and the optically active bis phosphine ligand.
Claim 38
Dependent Claim
12 words
A catalyst according to claim 35 wherein the transition metal is rhodium.
Claim 39
Dependent Claim
33 words
A catalyst according to claim 9 wherein the catalyst comprises a solution of a transition metal selected from the group consisting of rhodium, iridium and ruthenium and the optically active bis phosphine ligand.
Claim 40
Dependent Claim
12 words
A catalyst according to claim 37 wherein the transition metal is rhodium.
Claim 41
Dependent Claim
33 words
A catalyst according to claim 11 wherein the catalyst comprises a solution of a transition metal selected from the group consisting of rhodium, iridium and ruthenium and the optically active bis phosphine ligand.
Claim 42
Dependent Claim
12 words
A catalyst according to claim 39 wherein the transition metal is rhodium.
Claim 43
Dependent Claim
33 words
A catalyst according to claim 13 wherein the catalyst comprises a solution of a transition metal selected from the group consisting of rhodium, iridium and ruthenium and the optically active bis phosphine ligand.
Claim 44
Dependent Claim
12 words
A catalyst according to claim 41 wherein the transition metal is rhodium.
Claim 45
Dependent Claim
12 words
Cyclooctadiene-1,5-[1,2-bis(o-anisylphenylphosphino) ethane] rhodium tetrafluoroborate provided that the 1,2-bis(o-anisylphenylphosphino) ethane is optically active.
Claim 46
Dependent Claim
12 words
Cyclooctadiene-1,5-[1,2-bis(o-anisylphenylphosphino) ethane] rhodium tetrafluoroborate provided that the 1,2-bis(o-anisylphenylphosphino) ethane is optically active.
Claim 47
Dependent Claim
13 words
A catalyst solution containing (a) bis (cyclooctadiene-1,5)-dichlorodirhodium and (b) optically active 1,2-bis(o-anisylphenylphosphino) ethane.
Claim 48
Dependent Claim
13 words
A catalyst solution containing (a) bis (cyclooctadiene-1,5)-dichlorodirhodium and (b) optically active 1,2-bis(o-anisylphenylphosphino) ethane.
Claim 49
Dependent Claim
21 words
A solution according to claim 44 wherein the mole ratio of (a) to (b) is from about 0.25 to about 1.
Claim 50
Dependent Claim
17 words
A solution according to claim 45 wherein the mole ratio of (a) to (b) is about 0.5.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-03-05 | 1982-09-04 | 1983-03-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-03-05 | 1986-09-04 | 1987-03-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-03-05 | 1990-09-04 | 1991-03-06 | $7700.00 | Window Closed / Lapsed |