Rh-Catalyzed [3+2] Cycloaddition of 1-Sulfonyl-1,2,3-triazoles: Access to the Framework of Aspidosperma and Kopsia Indole Alkaloids

Rh-Catalyzed [3+2] Cycloaddition of 1-Sulfonyl-1,2,3-triazoles: Access to the Framework of Aspidosperma and Kopsia Indole Alkaloids
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Rh 催化的 [3 2] 1-磺酰基-1,2,3-三唑的环加成:接近 Aspidosperma 和 Kopsia 吲哚生物碱的框架

DOI:
10.1021/acs.orglett.6b01968
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发表时间:
2016-08-19
期刊:
影响因子:
5.2
通讯作者:
Zhai, Hongbin
Zhai, Hongbin
中科院分区:
化学1区
文献类型:
--
作者:
Li, Yun;Zhang, Qingyu;Zhai, Hongbin

文献摘要

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发展了一种Rh(II)催化的脱芳族分子内[3+2]偶极环加成反应,涉及吲哚C2-C3碳-碳双键。反应从底物中的三氮唑基团开始,在温和的条件下高效进行,可以容忍广泛的官能团。这些特点使当前的反应成为合成多环吲哚生物碱的非常有用的工具,如无子实体和相关生物碱的核心结构的快速组装所表明的那样。
A Rh(II)-catalyzed dearomative intramolecular [3 + 2] dipolar cycloaddition involving the indolic C2-C3 carbon-carbon double bond has been developed. The reaction was launched from the triazole moiety within the substrate and proceeded efficiently under mild conditions., A wide range of functional groups could be tolerated. These features render the current reaction a highly useful tool for the synthesis of polycyclic indole alkaloids, as showcased by a rapid assembly of the core structure of Aspidosperma and the related alkaloids.