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

被引：26

作者：

Takeda, Takuya ^{[1
]}

Harada, Shinji ^{[1
,2
]}

Okabe, Akito ^{[1
]}

Nishida, Atsushi ^{[1
,2
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2638522, Japan

[2] Chiba Univ, Mol Chiral Res Ctr, Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

基金：

日本学术振兴会;

关键词：

CASCADE SYNTHESIS; ORGANIC-SYNTHESIS; ALKYNES; ALKENYLATION; DERIVATIVES; ALKALOIDS; ARENES; CYCLIZATION; INHIBITORS; POTENT;

D O I：

10.1021/acs.joc.8b01407

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 pi-Lewis acid and sigma-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.

引用

页码：11541 / 11551

页数：11

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