Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 18, Pages 4565-4572Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900044
Keywords
heterocycles; iminium compounds; Lewis acids; metathesis; molecular diversity
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Funding
- MEC [CTQ2006-10930/BQU]
- CAM-UCM [920234]
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The cerium(IV) ammonium nitrate (CAN) catalyzed, four-component reaction between primary aliphatic amines, beta-ketoesters or beta-ketothioesters, alpha,beta-unsaturated aldehydes, and alcohols provided a very efficient and atom-economical access to substituted 6-alkoxy-2-methyl-1,4,5,6-tetrahydropyridines. These materials were then transformed into homoquinolizine derivatives in excellent yields by using a two-step sequence comprised of regioselective gamma-deprotonation-allylation and ring-closing metathesis reactions. The possibility of displacing the alkoxy group by allylsilane nucleophiles, presumably through a vinylogous acyliminium intermediate species, was also demonstrated.
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