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硫脲-季铵盐催化亚胺酯的不对称1,3-偶极环加成反应构建螺[吡咯烷-3,3'-氧化吲哚]

Thiourea-Quaternary Ammonium Salt Catalyzed Asymmetric 1, 3-Dipolar Cycloaddition of Imino Esters To Construct Spiro[pyrrolidin-3,3'-oxindoles].

作者信息

Zhang Jia-Xing, Wang Hong-Yu, Jin Qiao-Wen, Zheng Chang-Wu, Zhao Gang, Shang Yong-Jia

机构信息

Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University , Wuhu, Anhui 241000, China.

Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

出版信息

Org Lett. 2016 Oct 7;18(19):4774-4777. doi: 10.1021/acs.orglett.6b02098. Epub 2016 Sep 14.

Abstract

A highly enantioselective 1,3-dipolar cycloaddition of imino esters with methyleneindolinones has been realized by using readily available thiourea-quaternary ammonium salts as phase-transfer catalysts, enabling efficient construction of a range of chiral spiro[pyrrolidin-3,3'-oxindoles] in good yields with excellent enantioselectivities under mild conditions.

摘要

通过使用易于获得的硫脲-季铵盐作为相转移催化剂,实现了亚氨基酯与亚甲基吲哚酮的高度对映选择性1,3-偶极环加成反应,能够在温和条件下以良好的产率和优异的对映选择性高效构建一系列手性螺[吡咯烷-3,3'-氧化吲哚]。

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