Mannich-Michael versus formal aza-Diels-Alder approaches to piperidine derivatives

A review into the aza-Diels-Alder reaction, mainly concentrating on literature examples that form piperidin-4-ones from the reaction of imines and electron rich dienes or enones, either through a Lewis acidic/Brønsted acid approach or through the use of an organocatalyst. This review questions wheth...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2011-05, Vol.9 (9), p.3105-3121
Main Authors: Girling, P Ricardo, Kiyoi, Takao, Whiting, Andrew
Format: Article
Language:English
Subjects:
Aza Compounds - chemistry
Catalysis
Oxidation-Reduction
Piperidines - chemistry
Stereoisomerism
Thermodynamics
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Summary:A review into the aza-Diels-Alder reaction, mainly concentrating on literature examples that form piperidin-4-ones from the reaction of imines and electron rich dienes or enones, either through a Lewis acidic/Brønsted acid approach or through the use of an organocatalyst. This review questions whether the mechanism of the aza-Diels-Alder reaction is step wise as opposed to concerted when using oxygenated dienes.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob00996b