Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch

被引：18

作者：

Ciccolini, Cecilia ^{[1
]}

Mari, Giacomo ^{[1
]}

Gatti, Francesco G. ^{[2
]}

Gatti, Giuseppe ^{[1
]}

Giorgi, Gianluca ^{[3
]}

Mantellini, Fabio ^{[1
]}

Favi, Gianfranco ^{[1
]}

机构：

[1] Univ Urbino Carlo Bo, Dept Biomol Sci, Sect Chem & Pharmaceut Technol, I-61029 Urbino, Italy

[2] Dept Chem Mat & Chem Engn G Natta, I-20133 Milan, Italy

[3] Univ Siena, Dept Biotechnol Chem & Pharm, I-53100 Siena, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 17期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; CATALYTIC ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; METAL-IONS; CONSTRUCTION; HETEROCYCLES; 1,2-DIAZA-1,3-DIENES; TRYPTAMINES; DERIVATIVES; ALKALOIDS;

D O I：

10.1021/acs.joc.0c01489

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zn(II)-catalyzed divergent synthesis of functionalized polycyclic indolines through formal [3 + 2] and [4 + 2] cycloadditions of indoles with 1,2-diaza-1,3-dienes (DDs) is reported. The nature and type of substituents of substrates are found to act as a chemical switch to trigger two distinct reaction pathways and to obtain two different types of products upon the influence of the same catalyst. The mechanism of both [4 + 2] and [3 + 2] cycloadditions was investigated and fully rationalized by density functional theory (DFT) calculations.

引用

页码：11409 / 11425

页数：17

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[3]

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