One??Pot Synthesis of Orthogonally Protected Enantiopure S??(Aminoalkyl) cysteine Derivatives

…, D Guarino, L Longobardo, R Caputo

Index: Bolognese, Adele; Fierro, Olga; Guarino, Daniela; Longobardo, Luigi; Caputo, Romualdo European Journal of Organic Chemistry, 2006 , # 1 p. 169 - 173

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Citation Number: 12

Abstract

Abstract The general synthesis of a new class of non-natural diamino acids, 2-amino-3-[(2′- aminoalkyl) thio] propanoic acids or S-(aminoalkyl) cysteines, is reported. Under the conditions devised, enantiopure N-Boc-protected β-iodoamines, readily generated from proteinogenic α-amino acids, are treated with L-cysteine ethyl ester hydrochloride, using Cs 2 CO 3 as a base. The S-alkylation products, obtained in high yields (96–98%) and ...