Catalytic Aza-Wacker Annulation: Tuning Mechanism by the Activation Mode of Amide and Enantioselective Syntheses of Melinonine-E and Strychnoxanthine

Catalytic Aza-Wacker Annulation: Tuning Mechanism by the Activation Mode of Amide and Enantioselective Syntheses of Melinonine-E and Strychnoxanthine
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催化 Aza-Wacker 环化:酰胺激活模式的调节机制以及 Melinonine-E 和马钱子黄嘌呤的对映选择性合成

DOI:
10.1021/acs.orglett.8b00725
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发表时间:
2018
期刊:
影响因子:
5.2
通讯作者:
Hong Ran
Hong Ran
中科院分区:
化学1区
文献类型:
--
作者:
Xie Chanmin;Luo Jisheng;Zhang Yuping;Huang Sha-Hua;Zhu Lili;Hong Ran

文献摘要

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发现了一个前所未有的酰胺的N-取代基对于环化反应的成功至关重要,从而以较高的产率建立了2-氮杂双环[3.3.1]壬烷和其他环状骨架。在甜蜜素-E和士的诺黄嘌呤的简明合成和绝对构型测定中,进一步说明了新的催化氮杂-瓦克环化方法。
An unprecedented N-substituent of the amide was found to be crucial for the successful annulation to establish 2-azabicyclo[3.3.1]nonane and other ring skeletons in good yield. The novel catalytic aza-Wacker annulation methodology was further illustrated in the concise syntheses and the absolute configuration determinations of melinonine-E and strychnoxanthine.