Synthesis of Chiral Bicyclic Bis??lactam Components for the controlled self??assembly of hydrogen??bonded arrays

…, J Gabard, M Leclercq, JM Lehn, M Chevé

Index: Brienne, Marie-Josephe; Gabard, Jacqueline; Leclercq, Martine; Lehn, Jean-Marie; Cheve, Michel Helvetica Chimica Acta, 1997 , vol. 80, # 3 p. 856 - 875

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Citation Number: 15

Abstract

Abstract The chiral biyclic bis-lactams of structures 3 and 4 were synthesized from the key intermediate 2′ b, the N, N′-bis (4-methoxybenzyl) derivative of 2 (X= MeO)(Scheme 6). The synthesis of this intermediate involved two key steps:(1) a double condensation of glyoxylic acid/anisamide (= oxoacetic acid/4-methoxybenzamide) adduct 11c with veratrole (1, 2-dimethoxybenzene; 10) allowed the introduction of two glycine units at the 4, 5- ...