Asymmetric Reactions. IV. An Attempted Asymmetric Reduction by a Solution of [Co(CN)5]3− and Optically Active α-Amino Acid, and Its Reactive Species

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Abstract
Reduction of various olefines by a solution of pentacyanocobaltate and glycine or optically active α-amino acid was studied. There is no essential difference between the reactivity of [Co(CN)5H]3− to olefines and that of the solution of pentacyanocobaltate and α-amino acid. Atropic acid was reduced with the solution containing optically active α-amino acid (l-isoleucine) to give slightly optically active hydratropic acid. It was found that the main reactive species in the solution of [Co(CN)5]3− and α-amino acid was [Co(CN)5H]3− (this might be the reason for the asymmetric reduction not taking place effectively), and the reversible change between [Co(CN)5]3− and [Co-(CN)5H]3− was observed depending on the pH of the solution.