Preparation of amino acids in high optical yield via catalytic h

Details Preparation of amino acids in high optical yield via catalytic h Preparation of amino acids in high optical yield via catalytic h

1981-03-16

1984-01-03

Wong, Jr., Harry

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

5253267, 525370, 526263, 502159, 502162, C08F 842, C08F22034

Patent

active

044243120

ABSTRACT:
Two new optically active pyrrolidinephosphine monomers prepared by the reaction of 2(S), 4(S)-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine and 2(R), 4(R)-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine with acryloyl-chloride to give N-acryloyl-2(S), 4(S)-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine (1) and N-acryloyl-2(R), 4(R)-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine (2). Copolymerization of 1 and 2 with hydrophilic comonomers and a divinyl monomer provided crosslinked insoluble polymers containing about 3-5% of 1 or 2 that would swell in polar solvents. Exchange of rhodium(I) onto the polymer gave catalysts which were active for the asymmetric hydrogenation of N-acyl-amino acids in high optical yields, the phosphine derived from the enantiomer of the naturally occurring 4-hydroxyproline giving S-amino acids.

REFERENCES:
patent: 2728739 (1955-12-01), Jones

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