From a spin-off to the advantageous use in Diels-Alder reactions: a combined synthetic, spectroscopic and computational approach to N-(dienyl)acylamines.
The acid-catalyzed condensation of aldehydes and acetamide has been shown to provide a pool of diverse equilibrating species. For the first time, the synthesis of substituted 1-N-acylamino-1,3-butadienes has been accomplished directly in moderate yields upon telomerization of two molecules of aldehyde with one molecule of carboxamide. Detailed spectroscopic and computational investigations establish the favourable formation of all-trans aminodienes under the reaction conditions. Employment thereof as diene building blocks in Diels-Alder reactions allows for the synthesis of carbocyclic molecules with high stereocontrol.
Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V., Buchbinderstr. 5-6, 18055 Rostock, Germany.
Dirk
D
Gördes
Axel Jacobi
AJ
von Wangelin
Stefan
S
Klaus
Helfried
H
Neumann
Dirk
D
Strübing
Sandra
S
Hübner
Haijun
H
Jiao
Wolfgang
W
Baumann
Matthias
M
Beller