Synthesis of polycyclic spiroindolines by highly diastereoselective interrupted Ugi cascade reactions of 3-(2-isocyanoethyl)indoles

被引：54

作者：

Saya, Jordy M. ^{[1
,2
]}

Oppelaar, Barry ^{[1
,2
]}

Cioc, Razvan C. ^{[1
,2
]}

van der Heijden, Gydo ^{[1
,2
]}

Vande Velde, Christophe M. L. ^{[3
]}

Orrua, Romano V. A. ^{[1
,2
]}

Ruijter, Eelco ^{[1
,2
]}

机构：

[1] Vrije Univ Amsterdam, Dept Chem & Pharmaceut Sci, De Boelelaan 1108, NL-1081 HZ Amsterdam, Netherlands

[2] Vrije Univ Amsterdam, Amsterdam Inst Mol Med & Syst AIMMS, De Boelelaan 1108, NL-1081 HZ Amsterdam, Netherlands

[3] Univ Antwerp, Adv Reactor Technol, Fac Appl Engn, Groenenborgerlaan 171, B-2020 Antwerp, Belgium

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 84期

关键词：

MULTICOMPONENT REACTIONS; 3-COMPONENT CONDENSATION; TRITYL ISOCYANIDE; TRANSFORMATIONS; CHEMISTRY; ALDEHYDES; PYRAZINES; INDOLES; ACCESS;

D O I：

10.1039/c6cc07459f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a highly diastereoselective interrupted Ugi reaction to construct a broad range of structurally congested and stereo-chemically complex spiroindolines from tryptamine-derived isocyanides. The reaction is facilitated by using fluorinated alcohols (TFE or HFIP) as solvents and tolerates a broad range of amines, aldehydes and 2-isocyanoethylindoles to give polycyclic products in moderate to excellent yields.

引用

页码：12482 / 12485

页数：4

共 37 条

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