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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.

DOI:10.1039/c6cc09775h
PMID:28217784
Abstract

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).

摘要

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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