Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A 2K6, Canada.
J Org Chem. 2010 Feb 5;75(3):783-8. doi: 10.1021/jo902319h.
An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp(3)-Csp) catalyzed by copper with use of natural alpha-amino acids as starting materials is developed under neutral conditions with the production of CO(2) and H(2)O as the only byproducts. Various functionalized nitrogen-containing compounds were obtained by this method. In these processes, interesting regioselectivites of the alkylation were observed, which has been rationalized by the relative stability of proposed resonance structures based on computation methods.
一种有趣的醛酮诱导的铜催化的分子间串联脱羧-偶联(Csp(3)-Csp)反应,以天然α-氨基酸为原料,在中性条件下进行,反应的副产物只有 CO(2) 和 H(2)O。该方法可以得到各种官能化的含氮化合物。在这些过程中,观察到了烷基化的有趣的区域选择性,这可以通过基于计算方法的提议共振结构的相对稳定性来合理化。