Phenylglyoxylates, asymmetric reduction

Asymmetric reduction of a-keto esters, typically pyruvates and phenylglyoxylates, is effected by chiral rhodium complex-catalyzed hydrosilylation . Optical yields of lactates are higher than those obtained for simple prochiral ketones. The ester group as well as the hydrosilane used effects the extent of asymmetric induction. A high optical yield is attained for M-propyl pyruvate using a-naphthylphenylsilane (85.4% e.e.p ... 

Bonner, W.A. (1995) The quest for chirality, m. Physical origin of homochirality in life. Conference Proceedings, 379. Santa Monica, Cal., American Institute of Physies Press, Woodbury, N.Y., p. 17-49 Bonner, W.A. (1990) Attempted asymmetric electrochemical reductions in magnetic-fields. Origins of Life and Evolution of Biosphere 20,1-13 Bonner, W.A. (1990) The eleetrochemical reduction of phenylglyoxylic acid in a magnetic-field, Electrochem. Acta 35, 683-684. 

Fig. 1. Application of Prolog s rule to the reduction of (—)-menthyl phenylglyoxylate. Hydrogen is the small, —CHs— the medium, and —CH(CH3)2— the large group on the asymmetric carbon.

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