Asymmetric Dearomative (3+2)-Cycloaddition Involving Nitro-Substituted Benzoheteroarenes under H-Bonding Catalysis

Molecules

Anna Skrzyńska¹  Sebastian Frankowski¹  Łukasz Albrecht¹  Maciej Saktura¹  Sylwia Wódka¹ 

[1] Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland;

关键词: organocatalysis;    CADA reactions;    dearomative (3+2)-cycloaddition;    2-nitrobenzofurans;    azomethine ylides;   

DOI  :  10.3390/molecules26164992

来源: DOAJ

【 摘 要 】

In our studies, the organocatalytic 1,3-dipolar cycloaddition between 2-nitrobenzofurans or 2-nitrobenzothiophene and N-2,2,2-trifluoroethyl-substituted isatin imines has been developed. The reaction has been realized by employing bifunctional organocatalysis, with the use of squaramide derivative being crucial for the stereochemical efficiency of the process. The usefulness of the cycloadducts obtained has been confirmed in selected transformations, including aromative and non-aromative removal of the nitro group.

【 授权许可】

Unknown