Rapid construction of tetrahydropyridine scaffolds via formal imino Diels–Alder reactions of Schiff bases and Nazarov reagents
Rapid construction of tetrahydropyridine scaffolds via formal imino Diels–Alder reactions of Schiff bases and Nazarov reagents
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通过席夫碱和纳扎罗夫试剂的正式亚氨基狄尔斯-阿尔德反应快速构建四氢吡啶支架
DOI：
10.1039/c9ob01880h
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发表时间：
2019
期刊：
影响因子：
--
通讯作者：
Rawal, V. H.
中科院分区：
文献类型：
--
作者：
Wu, Y. -K.;Rawal, V. H.
描述了一种合成高度官能化的哌啶的一瓶两步法。该过程涉及Schiff碱和Nazarov试剂的正式[4 + 2]环加成，然后是初始环加成物的简单阐述。值得注意的是，这些氮杂环化通过质子溶剂促进，并且在环境条件下顺利进行，而无需其他添加剂。通过（±）-丁苯那嗪的简洁、收敛的合成进一步展示了该成环方案的合成效用。
Described is a one-flask, two-step method for the synthesis of highly functionalized piperidines. The process involves formal [4 + 2] cycloadditions of Schiff bases and Nazarov reagents, followed by facile elaborations of the initial cycloadducts. Notably, these aza-annulations are facilitated by protic solvents and proceed smoothly under ambient conditions, without other additives. The synthetic utility of this annulation protocol is further showcased through a concise, convergent synthesis of (±)-tetrabenazine.