Enantioselective Syntheses of 4H-3,1-Benzoxazines via Catalytic Asymmetric Chlorocyclization of o-Vinylanilides

Enantioselective Syntheses of 4H-3,1-Benzoxazines via Catalytic Asymmetric Chlorocyclization of o-Vinylanilides
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通过邻乙烯基苯胺催化不对称氯环化对映选择性合成 4H-3,1-苯并恶嗪

DOI:
10.1021/acs.joc.9b02395
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发表时间:
2019
期刊:
The Journal of Organic Chemistry
影响因子:
--
通讯作者:
Jun Deng
Jun Deng
中科院分区:
其他
文献类型:
--
作者:
Qinxia Xie;Hai-Jiao Long;Qiong-Yin Zhang;Pei Tang;Jun Deng

文献摘要

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烯烃的催化不对称卤环化反应是合成手性杂环化合物的一种有效而直接的方法。本文报道了一种有效的手性苯并恶嗪衍生物的合成方法--邻乙烯基苯胺的有机催化氯环化反应。该方法提供了一系列的手性苯并恶嗪,产率良好至优异(高达99%产率)和高水平的对映体控制(高达92%ee)。
The catalytic asymmetric halocyclization of alkene is a powerful and straightforward strategy for the synthesis of chiral heterocyclic compounds. Herein, an effective approach to chiral benzoxazine derivatives through organocatalyzed chlorocyclization ofo-vinylanilides was reported. This method provides facile access to a series of chiral benzoxazines in good to excellent yields (up to 99% yield) and with high-level enantiocontrol (up to 92% ee).