Asymmetric hydrogenation. Rhodium chiral bisphosphine catalyst

BD Vineyard, WS Knowles, MJ Sabacky…

Index: Vineyard,B.D. et al. Journal of the American Chemical Society, 1977 , vol. 99, p. 5946 - 5952

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Citation Number: 776

Abstract

Abstract: Enantiomeric excesses of 95-96% are obtained by the asymmetric hydrogenation of a-acylaminoacrylic acids. The olefin configuration, whether E or Z, has a profound influence on the rate and stereospecificity. Excellent selectivity (-90% ee) was obtained with an a-enol ester, which is the first outstanding result with a nonamide substrate. A catalyst picture is presented and the stereochemical results are discussed.