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Synthesis 2014; 46(02): 135-157
DOI: 10.1055/s-0033-1338581
DOI: 10.1055/s-0033-1338581
review
Catalytic Asymmetric Aza-Diels–Alder Reactions: The Povarov Cycloaddition Reaction
Further Information
Publication History
Received: 01 August 2013
Accepted after revision: 06 September 2013
Publication Date:
10 December 2013 (online)
Abstract
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 Brønsted 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
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Comprehensive reviews on the synthesis of THQ and its biological significance:
Recent reviews on Povarov reactions:
See, for example:
Reviews:
Reviews:
Reviews:
For reviews on multicatalytic, domino, sequential and relay processes, see:
Reviews:
Reviews: