US4123465A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Chiral tertiary phosphines
Assignee: Hoffmann La Roche Inc
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Filing: 1977-08-10
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Granted: 1978-10-31
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Expires: 1997-08-10
Abstract
Abstract A method for the homogeneous catalytic enantioselective hydrogenation of alkyl and alkenyl substituted acrylic acids wherein these acids are selectively hydrogenated at the double bond alpha,beta to the acid function, said hydrogenations are catalyzed by rhodium complexes of chiral tertiary phosphines. This method provides a route to chiral dihydrogeranic acid and other intermediates useful in the synthesis of chiral vitamin E, citronellal, and menthol. Novel chiral tertiary phosphines are also disclosed.
Inventors
- 👤 Donald H. Valentine, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 07:01
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/50; C07F9/5031; C07C; C07C45/00; C07C45/61; C07C45/62; C07C51/00; C07C51/16; C07C51/295; C07C51/347; C07C51/36; C07C53/00; C07C53/126; C07C53/128; C07C57/00; C07C57/02; C07C57/03; C07F9/5022; C07F9/547; C07F9/655; C07F9/65515; Y; Y10; Y10S; Y10S260/00; Y10S260/44
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
93 words
A chiral phosphine of the formula: ##STR10## wherein R 7 is methyl, isopropyl, xylyl, mesityl, benzyl, aryl or a substituted aryl selected from the group consisting of tolyl, ethylphenyl, cyclohexylphenyl, dimethylphenyl and methoxyphenyl; R 8 is lower alkyl, aryl or a substituted aryl selected from the group consisting of tolyl, dimethylphenyl and methoxyphenyl; R 9 is hydrogen, alkyl, hydroxylalkyl, aminoalkyl, perfluoroalkyl, aryl or methoxyphenyl; R 10 is hydrogen, alkyl, aryl, hydroxyalkyl, aminoalkyl or perfluoroalkyl, with the proviso that R 9 and R 10 must be different; R 11 is hydrogen, alkyl or aryl.
Claim 2
Dependent Claim
93 words
A chiral phosphine of the formula: ##STR10## wherein R 7 is methyl, isopropyl, xylyl, mesityl, benzyl, aryl or a substituted aryl selected from the group consisting of tolyl, ethylphenyl, cyclohexylphenyl, dimethylphenyl and methoxyphenyl; R 8 is lower alkyl, aryl or a substituted aryl selected from the group consisting of tolyl, dimethylphenyl and methoxyphenyl; R 9 is hydrogen, alkyl, hydroxylalkyl, aminoalkyl, perfluoroalkyl, aryl or methoxyphenyl; R 10 is hydrogen, alkyl, aryl, hydroxyalkyl, aminoalkyl or perfluoroalkyl, with the proviso that R 9 and R 10 must be different; R 11 is hydrogen, alkyl or aryl.
Claim 3
Dependent Claim
11 words
The chiral phosphine of claim 1 wherein R 7 is phenyl.
Claim 4
Dependent Claim
11 words
The chiral phosphine of claim 2 wherein R 8 is phenyl.
Claim 5
Dependent Claim
11 words
The chiral phosphine of claim 1 wherein R 9 is phenyl.
Claim 6
Dependent Claim
11 words
The chiral phosphine of claim 1 wherein R 10 is phenyl.
Claim 7
Dependent Claim
11 words
The chiral phosphine of claim 1 wherein R 11 is phenyl.
Claim 8
Dependent Claim
11 words
The chiral phosphine of claim 1 wherein R 7 is methoxyphenyl.
Claim 9
Dependent Claim
11 words
The chiral phosphine of claim 7 wherein R 8 is methoxyphenyl.
Claim 10
Dependent Claim
13 words
The chiral phosphine of claim 1 wherein said phosphine is chiral 2-phenyl-2-methoxyethyldiphenyl phosphine.
Claim 11
Dependent Claim
13 words
The chiral phosphine of claim 1 wherein said phosphine is chiral 2-phenoxypropyldiphenyl phosphine.
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-30 | 1982-05-01 | 1982-10-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-30 | 1986-05-01 | 1986-10-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-30 | 1990-05-01 | 1990-10-31 | $7700.00 | Window Closed / Lapsed |