Asymmetric Hydrogenation of C=O Double Bond with Modified Raney Nickel. XXII

概要

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The state of the amino acid molecule used as a modifying reagent on a catalyst surface was investigated. From the relationship between the asymmetric activities of the catalysts modified with L-valine and its derivatives and the stability constants of the nickel chelates of L-valine and its derivatives, it was concluded that L-valine adsorbs like a ligand of the chelate on the catalyst surface. This conclusion was also supported by the finding that the asymmetric activity of the catalyst modified with the nickel L-valine chelate was higher than those of the catalysts modified with L-valine and its derivatives. Also, the asymmetric activities of the catalysts modified with L-histidine, L-serine, and L-proline, and with the nickel chelates of the above three L-amino acids were discussed on the basis of the stability constants of the nickel chelates of the above three L-amino acids, it was concluded that two conditions at least are necessary for the modifying reagent to be effective; it must adsorb stably on the catalyst surface, and it must have a structure affording effective asymmetric control of the substrate.
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