手性布朗斯特酸催化的对映选择性α-酰胺烷基化反应：一项实验与预测相结合的研究。
Chiral Brønsted Acid-Catalyzed Enantioselective α-Amidoalkylation Reactions: A Joint Experimental and Predictive Study.
作者信息
Aranzamendi Eider, Arrasate Sonia, Sotomayor Nuria, González-Díaz Humberto, Lete Esther
机构信息
Departamento de Química Orgánica II Facultad de Ciencia y Tecnología Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU) Apdo. 644 48080 Bilbao Spain.
Departamento de Química Orgánica II Facultad de Ciencia y Tecnología Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU) Apdo. 644 48080 Bilbao Spain; IKERBASQUE Basque Foundation for Science 48080 Bilbao Spain.
出版信息
ChemistryOpen. 2016 Nov 23;5(6):540-549. doi: 10.1002/open.201600120. eCollection 2016 Dec.
Enamides with a free NH group have been evaluated as nucleophiles in chiral Brønsted acid-catalyzed enantioselective α-amidoalkylation reactions of bicyclic hydroxylactams for the generation of quaternary stereocenters. A quantitative structure-reactivity relationship (QSRR) method has been developed to find a useful tool to rationalize the enantioselectivity in this and related processes and to orient the catalyst choice. This correlative perturbation theory (PT)-QSRR approach has been used to predict the effect of the structure of the substrate, nucleophile, and catalyst, as well as the experimental conditions, on the enantioselectivity. In this way, trends to improve the experimental results could be found without engaging in a long-term empirical investigation.
具有游离NH基团的烯酰胺已被评估为亲核试剂，用于双环羟基内酰胺的手性布朗斯特酸催化对映选择性α-酰胺烷基化反应，以生成季碳立体中心。已开发出一种定量结构-反应活性关系（QSRR）方法，以找到一种有用的工具，用于合理化此过程及相关过程中的对映选择性，并指导催化剂的选择。这种相关微扰理论（PT）-QSRR方法已用于预测底物、亲核试剂和催化剂的结构以及实验条件对映选择性的影响。通过这种方式，无需进行长期的实证研究就能找到改善实验结果的趋势。
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