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

Organic & biomolecular chemistry (2011-03-11)
P Ricardo Girling, Takao Kiyoi, Andrew Whiting
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Piperidine, ReagentPlus®, 99%
Sigma-Aldrich
Piperidine, ≥99.5%, purified by redistillation
Sigma-Aldrich
Piperidine solution, suitable for peptide synthesis, 20% in DMF
Sigma-Aldrich
Piperidine, biotech. grade, ≥99.5%
Sigma-Aldrich
Piperidine, puriss. p.a., ≥99.0% (GC/T)

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