Dipartimento di Farmacia, Università di Salerno , Via Giovanni Paolo II 132, 84084 Fisciano, Italy.
Dipartimento di Farmacia, Università di Napoli "Federico II" , Via Montesano 49, 80131 Napoli, Italy.
J Org Chem. 2017 Dec 1;82(23):12014-12027. doi: 10.1021/acs.joc.7b01656. Epub 2017 Nov 14.
An acid- and oxidant-promoted intramolecular cyclization of a tetrahydro-β-carboline-based dipeptide has been developed to prepare new indole-fused aminoacetals. This approach involves N-acyliminium formation from readily available precursors and cyclization under mild reaction conditions. The diastereoselectivity in the formation of the products is influenced by the specific substituents of the starting reagents, which has been rationalized analyzing the energy profile of the related reactions and the relative stability of the proposed structures based on DFT computational methods.
已开发出一种基于四氢-β-咔啉二肽的酸和氧化剂促进的分子内环化反应，以制备新的吲哚稠合氨基缩醛。该方法涉及从易得的前体形成 N-酰亚胺离子，并在温和的反应条件下环化。产物形成的非对映选择性受起始试剂的特定取代基的影响，通过分析相关反应的能量曲线和基于 DFT 计算方法的提议结构的相对稳定性，对其进行了合理化解释。
