No.135
P Chiral Ligand
| B3035 | (R,R)-DIPAMP [=(R,R)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane] (1a) |
100mg 1g |
| B3036 | (S,S)-DIPAMP [=(S,S)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane] (1b) |
100mg 1g |
Compound 1 are P-chiral ligands developed by Knowles et al. This compound 1 forms a stable complex with rhodium, and the complex has been used as a catalyst for an asymmetric hydrogenation reaction. Particularly, the asymmetric hydrogenation reaction of α-acetylamino cinnamic acid derivative 2 is well known, and it provides L-amino acid derivative 3 with high optical purity. When this compound 3 is de-protected, L-DOPA, which is used for the treatment of Parkinsonism, can be obtained. Knowles won the Nobel Prize in Chemistry for his achievement of developing this asymmetric synthesis of L-DOPA in 2001.
References
1) Asymmetric hydrogenation with a complex of Rh and a chiral bisphosphine
a) W. S. Knowles, M. J. Sabacky, B. D. Vineyard, D. J. Weinkauff, J. Am. Chem. Soc., 1975, 97, 2567; b) B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachman, D. J. Weinkauff, J. Am. Chem. Soc., 1977, 99, 5946.
a) W. S. Knowles, M. J. Sabacky, B. D. Vineyard, D. J. Weinkauff, J. Am. Chem. Soc., 1975, 97, 2567; b) B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachman, D. J. Weinkauff, J. Am. Chem. Soc., 1977, 99, 5946.
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