Stereoselective Synthesis of 2, 4-Diamino Acids by Asymmetric Hydrogenation

NG Park, S Lee, H Maeda, H Aoyagi…

Index: Park, Nam Gyu; Lee, Sannamu; Maeda, Hiroshi; Aoyagi, Haruhiko; Kato, Tetsuo Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 7 p. 2315 - 2319

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Citation Number: 13

Abstract

A stereoselective synthesis of unusual basic amino acids, ornithine, 2, 4-diaminopentanoic acid, and 2, 4-diamino-6-methylheptanoic acid, was achieved by the hydrogenation of cyclic α, β-dehydro dipeptides obtained by the condensation of cyclo (–Gly–L (or D)-aminoacyl–) and protected linear or chiral amino aldehydes. The degree of chiral induction greatly depended on the bulkiness of the side chains of α, β-dehydro amino acids. The R f values ...