Stereoselective synthesis of 2, 3-diamino acids. 2, 3-Diamino-4-phenylbutanoic acid

PJ Dunn, R Haener, H Rapoport

Index: Dunn, Peter J.; Haener, Robert; Rapoport, Henry Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 5017 - 5025

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Citation Number: 90

Abstract

The synthesis of (2S, 3S)-and (2S, 3R)-2, 3-diamino-4-phenylbutanoic acid (IC and 3) from L- aspartic acid is described. The N-(phenylfluorenyl)-prote&d aspartic acid diesters 4 and 10 (a-tert-butyl,@-methyl), 18@-benzyl, a-tert-butyl), and 28 (@-benzyl, a-methyl) are regioselectively benzylated at C-3 by using KHMDS and benzyl bromide or iodide. Whereas the alkylation of compounds 4 and 28 proceeds in low to moderate diastereoselectivities, ...