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环丙烷-1,1-二酯与α,β-不饱和羰基化合物的协同光/路易斯酸催化串联分子内[3 + 2]交叉环加成反应合成中等大小碳环化合物

Cooperative Photo-/Lewis Acid Catalyzed Tandem Intramolecular [3 + 2] Cross-Cycloadditions of Cyclopropane 1,1-Diesters with α,β-Unsaturated Carbonyls for Medium-Sized Carbocycles.

作者信息

Wang Zhenjun, Chen Shuai, Ren Jun, Wang Zhongwen

机构信息

State Key Laboratory and Institute of Elemento-Organic Chemistry, Synergetic Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , 94 Weijin Road, Tianjin 300071, P.R. China.

出版信息

Org Lett. 2015 Sep 4;17(17):4184-7. doi: 10.1021/acs.orglett.5b01928. Epub 2015 Aug 27.

Abstract

A tandem isomerization/intramolecular [3 + 2] cross-cycloaddition (IMCC) of cyclopropane 1,1-diesters with α,β-unsaturated ketones/aldehydes under a cooperative catalysis of photo and Lewis acids has been successfully developed. This supplied a general and efficient strategy for construction of medium-sized carbocyclic (8-, 9-, and 10-membered) skeletons as well as such carbocycle-based bridged oxa-bicyclo[n.2.1] (n = 4-6) skeletons.

摘要

在光和路易斯酸的协同催化下,环丙烷1,1 - 二酯与α,β - 不饱和酮/醛的串联异构化/分子内[3 + 2]交叉环加成反应(IMCC)已成功开发。这为构建中等大小的碳环(8、9和10元)骨架以及此类基于碳环的桥连氧杂双环[n.2.1](n = 4 - 6)骨架提供了一种通用且有效的策略。

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