# US 4,397,787 A · Rhodium complexes containing chiral phosphine ligands useful as hydrogenation catalysts

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- Number: US 4,397,787 A
- Document ID: US4397787A
- Status: Granted
- Kind: A
- Application number: 06/340,443
- Filed: 1982-01-18
- Granted: 1983-08-09
- Earliest claimed: 1980-03-19
- Assignees: The Procter & Gamble Company
- Inventors: Dennis P. Riley
- Web page: https://patentgrep.com/patent/US4397787A

## CPC

- C07F 15/00: Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- B01J 31/2291: {Olefins}
- B01J 31/2295: {Cyclic compounds, e.g. cyclopentadienyls}
- B01J 31/2409: {with more than one complexing phosphine-P atom}
- B01J 31/2414: {comprising aliphatic or saturated rings}
- C07C 29/147: of carboxylic acids or derivatives thereof
- C07C 51/36: by hydrogenation of carbon-to-carbon unsaturated bonds
- C07D 209/20: substituted additionally by nitrogen atoms, e.g. tryptophane
- C07F 9/5027: {Polyphosphines}
- C07F 15/0073: {Rhodium compounds}
- B01J 2231/645: of C=C or C-C triple bonds
- B01J 2531/821: Ruthenium
- B01J 2531/822: Rhodium
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Rhodium (1) complexes containing the chiral phosphine ligand (R)-1,2-bis(diphenylphosphino)-1-cyclohexylethane which are useful as chiral hydrogenation catalysts. These catalysts are especially useful in the chiral hydrogenation of alpha-acylamido acrylic acids.

## Claims

### Claim 1

A compound of the formula ##STR25## wherein M is a transition metal, R is a chelating diene, R.sub.1 is cyclohexyl, and A.sup.- is a non-coordinating anion.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein the transition metal is rhodium or ruthenium.

### Claim 3 (depends on 2)

A compound according to claim 2 wherein the chelating diene is norbornadiene.

### Claim 4 (depends on 2)

A compound according to claim 2 wherein the chelating diene is a 1,5-diene.

### Claim 5 (depends on 4)

A compound according to claim 4 wherein the 1,5-diene is 1,5-cyclooctadiene.

### Claim 6 (depends on 1)

A compound according to claim 1 wherein the non-coordinating anion is PF.sub.6.sup.-, BF.sub.4.sup.-, or ClO.sub.4.sup.-.

### Claim 7 (depends on 1)

A compound according to claim 1 wherein M is rhodium, R is norbornadiene, and A.sup.- is PF.sub.6.sup.-.

### Claim 8 (depends on 2)

A compound according to claim 2 wherein ##STR26## is the (R)- stereoisomer.

### Claim 9 (depends on 2)

A compound according to claim 2 wherein ##STR27## is the (S)- stereisomer.