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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
Abstract 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.