Preparation of amino acids in high optical yield via catalytic hydrogenation
US4424312A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Mar 16, 1981 |
| Grant date | Jan 3, 1984 |
| Priority date | — |
| Expiry date | Mar 16, 2001 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F9/572
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.