Catalytic Asymmetric Inverse‐Electron‐Demand 1,3‐Dipolar Cycloaddition of C,N‐Cyclic Azomethine Imines with Azlactones: Access to Chiral Tricyclic Tetrahydroisoquinolines | Zendy

Liu Xihong | Zendy; Wang Yijie | Zendy; Yang Dongxu | Zendy; Zhang Jinlong | Zendy; Liu Dongsheng | Zendy; Su Wu | Zendy

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Catalytic Asymmetric Inverse‐Electron‐Demand 1,3‐Dipolar Cycloaddition of C,N‐Cyclic Azomethine Imines with Azlactones: Access to Chiral Tricyclic Tetrahydroisoquinolines

Author(s) -

Liu Xihong,

Wang Yijie,

Yang Dongxu,

Zhang Jinlong,

Liu Dongsheng,

Su Wu

Publication year - 2016

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201602880

Subject(s) - enantioselective synthesis , cycloaddition , chemistry , bifunctional , tricyclic , combinatorial chemistry , 1,3 dipolar cycloaddition , catalysis , inverse , organic chemistry , mathematics , geometry

Reported herein is a bifunctional‐organocatalyst‐mediated enantioselective inverse‐electron‐demand 1,3‐dipolar cycloaddition of C,N‐cyclic azomethine imines with azlactones. The strategy provides concise access to enantioenriched C1‐substituted tetrahydroisoquinolines featuring a pyrazolidinone scaffold. Moreover, the scalability and practical utility of this protocol was well demonstrated by employing a gram‐scale reaction and some representative transformations.

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