Diastereoselective synthesis of functionalized tetrahydropyridazines containing indole scaffolds via an inverse-electron-demand aza-Diels-Alder reaction
Diastereoselective synthesis of functionalized tetrahydropyridazines containing indole scaffolds via an inverse-electron-demand aza-Diels-Alder reaction
复制标题
通过逆电子需求氮杂-狄尔斯-阿尔德反应非对映选择性合成含有吲哚支架的官能化四氢哒嗪
DOI：
10.1039/d1qo00623a
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发表时间：
2021-06-08
影响因子：
5.4
通讯作者：
Wang, Chun-Jiang
中科院分区：
文献类型：
--
作者：
Chen, Taotao;Che, Chao;Wang, Chun-Jiang
本文报道了一种新的无催化剂、碱促进的原位生成偶氮烯烃与3-乙烯基吲哚的反电子需求氮杂-Diels-桤木（IEDDA）反应。这种有效的方案提供了结构上重要的含有吲哚的四氢哒嗪支架，具有优异的结果（72%-89%产率，>20：1 dr）。此外，通过Cu/（S，S）-Pr-i-box体系初步实现了该反应的催化不对称化，得到了81%的手性产物，其dr>20：1，ee> 93%，环化产物还可以通过简单的转化进行功能化，得到其他有用的有机分子.
An unprecedented base-promoted and catalyst-free inverse-electron-demand aza-Diels-Alder (IEDDA) reaction between easily available in situ generated azoalkenes and 3-vinylindoles has been developed. This efficient protocol afforded structurally important tetrahydropyridazines containing indole scaffolds with excellent results (72%-89% yields, >20 : 1 dr). Moreover, the catalytic asymmetric version of this reaction was preliminarily realized through a Cu/(S,S)-Pr-i-box system to prepare the desired chiral product with 81% yield and >20 : 1 dr and 93% ee. The cyclization products could also be well functionalized to access other useful organic molecules through simple transformations.