Mechanistic studies on the formal aza-Diels-Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions.
The reaction of a para-methoxyaniline, ethyl glyoxalate-derived imine with a series of dienes has resulted in products, which initially suggest the operation of different modes of aza-Diels-Alder reaction. However, a more likely explanation is that a common reaction mechanism is operating, involving a step-wise Lewis-acid catalysed process, which only appears to behave similarly to alternative concerted cycloaddition reactions.
GlaxoSmithKline Medicines Research Centre, Stevenage, Herts, UK.
Stephen
S
Hermitage
Judith A K
JA
Howard
David
D
Jay
Robin G
RG
Pritchard
Michael R
MR
Probert
Andrew
A
Whiting
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D006575:Heterocyclic Compounds, 3-Ring; D007097:Imines