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Highly Enantioselective Synthesis of [1,2,4]Triazino[5,4-a]isoquinoline Derivatives via (3 + 3) Cycloaddition Reactions of Diazo Compounds and Isoquinolinium Methylides
Organic Letters ( IF 4.9 ) Pub Date : 2022-05-23 , DOI: 10.1021/acs.orglett.2c01122 Wei Wu 1 , Xiao Yan 2 , Xiaofeng Li 1 , Yanqiang Ning 1 , Lei Hu 1 , Lei Zhu 2 , Qin Ouyang 2 , Yungui Peng 1
Organic Letters ( IF 4.9 ) Pub Date : 2022-05-23 , DOI: 10.1021/acs.orglett.2c01122 Wei Wu 1 , Xiao Yan 2 , Xiaofeng Li 1 , Yanqiang Ning 1 , Lei Hu 1 , Lei Zhu 2 , Qin Ouyang 2 , Yungui Peng 1
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An array of chiral [1,2,4]triazino[5,4-a]isoquinoline derivatives were obtained in excellent yields (up to 98%) and with excellent enantioselectivities (up to 99% ee) via a new highly asymmetric (3 + 3) cycloaddition reaction of diazo compounds and isoquinolinium methylides, with a bifunctional chiral phase-transfer catalyst (PTC). Density functional theory calculations show that PTC has a bridge role in the deprotonation/protonation process. The obtained products were transformed into densely functionalized polycyclic heterocompounds with multiple stereocenters.
中文翻译：
通过重氮化合物和异喹啉鎓甲基化物的 (3 + 3) 环加成反应高对映选择性合成 [1,2,4] 三嗪 [5,4-a] 异喹啉衍生物
通过一种新的高度不对称（3 + 3) 使用双功能手性相转移催化剂 (PTC) 的重氮化合物和异喹啉鎓甲基化物的环加成反应。密度泛函理论计算表明，PTC 在去质子化/质子化过程中具有桥梁作用。所得产物转化为具有多个立体中心的密集官能化多环杂化合物。
更新日期：2022-05-23
中文翻译：
通过重氮化合物和异喹啉鎓甲基化物的 (3 + 3) 环加成反应高对映选择性合成 [1,2,4] 三嗪 [5,4-a] 异喹啉衍生物
通过一种新的高度不对称（3 + 3) 使用双功能手性相转移催化剂 (PTC) 的重氮化合物和异喹啉鎓甲基化物的环加成反应。密度泛函理论计算表明，PTC 在去质子化/质子化过程中具有桥梁作用。所得产物转化为具有多个立体中心的密集官能化多环杂化合物。
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