# US 4,393,240 A · Optically active phosphines

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- Number: US 4,393,240 A
- Document ID: US4393240A
- Status: Granted
- Kind: A
- Application number: 06/280,220
- Filed: 1981-07-06
- Granted: 1983-07-12
- Earliest claimed: 1981-07-06
- Inventors: John K. Stille
- Web page: https://patentgrep.com/patent/US4393240A

## CPC

- C07F 9/5027: {Polyphosphines}
- C07C 309/73: to carbon atoms of non-condensed six-membered aromatic rings
- C07F 15/0073: {Rhodium compounds}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The compounds (R)-1,2-bis(diphenylphosphino)-3-benzyloxypropane and (R)-1-tert-butoxy-2,3-bis(diphenylphosphino)propane are precursors to new rhodium-based asymmetric reaction catalysts having the formula: ##STR1## wherein R is benzyl or tert-butyl.

## Claims

### Claim 1

(R)-1,2-bis(diphenylphosphino)-3-benzyloxypropane.

### Claim 2

A process for producing (R)-1,2-bis(diphenylphosphino)-3-benzyloxypropane, comprising chemically reacting 1,2-O-ditosyl-3-O-benzyl-D-glycerol with sodium diphenylphosphine.

### Claim 3

(R)-1-tert-butoxy-2,3-bis(diphenylphosphino)propane.

### Claim 4

A process for producing (R)-1-tert-butoxy-2,3-bis(diphenylphosphino)propane, comprising chemically reacting (+)-1-tert-butyl-2,3-paratoluenesulfonyl glycerol with sodium diphenylphosphine to form an intermediate product, contacting said intermediate product sequentially with nickel(II) chloride and an alkali metal thiocyanate to form the complex [Ni(SCN)(bisphosphine)SCN], and contacting and reacting said complex with an alkali metal cyanide.

### Claim 5

(R)-1,2-bis(diphenylphosphino)propane-3-ol.

### Claim 6

A process for producing (R)-1,2-bis(diphenylphosphino)propane-3-ol, comprising chemically reacting (R)-1-tert-butoxy-2,3-bis(diphenylphosphino)propane with anhydrous trifluoroacetic acid to effect acid-catalyzed cleavage of the tert-butyl group.