Synthesis of N‐Heterocycles by Dehydrogenative Annulation of N‐Allyl Amides with 1,3‐Dicarbonyl Compounds

作者：Zheng‐Jian Wu, Shi‐Rui Li, Hai‐Chao Xu · 发表于：Angewandte Chemie International Edition · 年份：2018 · DOI：10.1002/anie.201807683 · 被引用次数：96 · 研究领域：Catalytic C–H Functionalization Methods、Asymmetric Synthesis and Catalysis、Asymmetric Hydrogenation and Catalysis

Dehydrogenative annulation under oxidizing reagent-free conditions is an ideal strategy to construct cyclic structures. Reported herein is an unprecedented synthesis of pyrrolidine and tetrahydropyridine derivatives through electrochemical dehydrogenative annulation of N-allyl amides with 1,3-dicarbonyl compounds. The electrolytic method employs an organic redox catalyst, which obviates the need for oxidizing reagents and transition-metal catalysts. In these reactions, the N-allyl amides serve as a four-atom donor to react with dimethyl malonate to give pyrrolidines by a (4+1) annulation, or with β-ketoesters to afford tetrahydropyridine derivatives by a (4+2) annulation.