Optically active phosphines

• US 4,393,240 A
• Filed: 07/06/1981
• Issued: 07/12/1983
• Est. Priority Date: 07/06/1981
• Status: Expired due to Fees

• Current Assignee: John K. Stille
• Original Assignee: John K. Stille
• Inventors: Stille, John K.
• Primary Examiner(s): Sneed, Helen M. S.
• Application Number:
  US06/280,220
• Time in Patent Office: 736 Days
• Field of Search: 260/429 R, 568/13
• US Class Current: 568/13
• CPC Class Codes: C07C 309/73 to carbon atoms of non-condensed six-membered aromatic rings
• CPC Class Codes: C07F 15/0073 Rhodium compounds
• CPC Class Codes: C07F 9/5027 Polyphosphines

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

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

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.

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

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.

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

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.