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通过[5 + 2]环加成反应合成环庚并[b]吲哚：双功能铟(III)催化的7元环稠合吲哚的立体选择性构建

Cyclohepta[ b]indole Synthesis through [5 + 2] Cycloaddition: Bifunctional Indium(III)-Catalyzed Stereoselective Construction of 7-Membered Ring Fused Indoles.

作者信息

Takeda Takuya, Harada Shinji, Okabe Akito, Nishida Atsushi

机构信息

Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1 Inohana, Chuo-ku , 263-8522 Chiba , Japan.

Molecular Chirality Research Center , Chiba University , 1-33 Yayoi-cho, Inage-ku , 263-8522 Chiba , Japan.

出版信息

J Org Chem. 2018 Oct 5;83(19):11541-11551. doi: 10.1021/acs.joc.8b01407. Epub 2018 Sep 11.

DOI:10.1021/acs.joc.8b01407
PMID:30179462
Abstract

A new approach for the synthesis of highly functionalized tetrahydrocyclohepta[ b]indoles through [5 + 2] cycloaddition was developed. Two carbon-carbon bonds were formed by the simple addition of an indium catalyst, which acted as both a π-Lewis acid and σ-Lewis acid to activate the alkyne and unsaturated ester, respectively. The reaction could be applied to various substrates and proceeded regio- and diastereoselectively in all cases.

摘要

开发了一种通过[5 + 2]环加成合成高官能化四氢环庚并[b]吲哚的新方法。通过简单添加铟催化剂形成两个碳-碳键，该铟催化剂分别作为π-路易斯酸和σ-路易斯酸来活化炔烃和不饱和酯。该反应可应用于各种底物，并且在所有情况下均具有区域选择性和非对映选择性。

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