Catalytic Asymmetric Aza-Diels-Alder Reactions: The Povarov Cycloaddition Reaction

被引:121
作者
Fochi, Mariafrancesca [1 ]
Caruana, Lorenzo [1 ]
Bernardi, Luca [1 ]
机构
[1] Alma Mater Studiorum Univ Bologna, Dept Ind Chem Toso Montanari, I-40136 Bologna, Italy
来源
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 02期
关键词
asymmetric catalysis; cycloaddition; heterocycles; multicomponent reaction; imines; CHIRAL BRONSTED ACID; N-ARYL IMINES; MULTICOMPONENT COUPLING REACTION; MANNICH-TYPE REACTION; PHOSPHORIC-ACID; ENANTIOSELECTIVE SYNTHESIS; LEWIS-ACID; TETRAHYDROQUINOLINE DERIVATIVES; QUINOLINE DERIVATIVES; EFFICIENT SYNTHESIS;
D O I
10.1055/s-0033-1338581
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Povarov reaction provides a straightforward and modular entry to 1,2,3,4- tetrahydroquinolines (THQs). Despite its importance, it was only very recently that several highly efficient catalytic asymmetric protocols for this reaction have been developed, as summarized in this review which falls on the 50th anniversary of Povarov's pioneering disclosure. Furthermore, this review collects and critically discusses the interrupted versions of the reaction, often featuring intriguing and still unclear mechanicistic pathways. 1 Introduction 2 Catalytic Asymmetric Povarov Cycloaddition Reactions 2.1 Chiral Lewis Acid Catalysis 2.2 Chiral Bronsted Acid Catalysis 2.2.1 Chiral Phosphoric Acid Catalyzed Povarov Cycloaddition Reactions 2.2.2 Chiral Urea Catalyzed Povarov Cycloaddition Reactions 3 Catalytic Asymmetric Interrupted Povarov Reactions 3.1 Intermolecularly Interrupted Povarov Reactions 3.2 Intramolecularly Interrupted Povarov Reactions 3.2.1 Interrupted Povarov Reactions with Salicyaldehyde-Derived Imines 3.2.2 Interrupted Povarov Reactions with Glyoxylic Acid Derived Imines 4 Conclusion
引用
收藏
页码:135 / 157
页数:23
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