布朗斯特酸催化的邻羟基苄醇与N,N'-环亚甲亚胺的立体选择性[4+3]环加成反应
Brønsted acid-catalyzed stereoselective [4+3] cycloadditions of ortho-hydroxybenzyl alcohols with N,N'-cyclic azomethine imines.
作者信息
Mei Guang-Jian, Zhu Zi-Qi, Zhao Jia-Jia, Bian Chen-Yu, Chen Jie, Chen Ruo-Wei, Shi Feng
机构信息
School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China.
出版信息
Chem Commun (Camb). 2017 Feb 28;53(18):2768-2771. doi: 10.1039/c6cc09775h.
The first [4+3] cycloaddition of ortho-hydroxybenzyl alcohols has been established by making use of N,N'-cyclic azomethine imines as suitable 1,3-dipoles under Brønsted acid catalysis. By using this strategy, biologically important seven-membered heterocyclic scaffolds have been constructed in good yields and excellent diastereoselectivities (up to 92% yield, most >95 : 5 dr).
通过利用N，N'-环亚甲胺亚胺作为合适的1,3-偶极子，在布朗斯特酸催化下实现了邻羟基苄醇的首例[4+3]环加成反应。采用该策略，已构建出具有重要生物学意义的七元杂环骨架，产率良好，非对映选择性优异（产率高达92%，大多数非对映体比例>95:5）。
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