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Tandem Diels–Alder cyclization/aromatization reactions of 5-vinyl-1-acyl-2-aryl-2,3-dihydro-4-pyridones

✍ Scribed by Jeffrey T. Kuethe; Daniel L. Comins

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
207 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A tandem Diels-Alder cyclization/aromatization of 5-vinyl-2,3-dihydro-4-pyridones and various dienophiles is reported. The intermediate Diels-Alder cycloadduct undergoes an elimination/aromatization to provide b-amino-ketones, b-amino-alcohols, and unnatural amino acids containing useful functionality.

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Inter- and intramolecular Horner–Wadsworth–Emmons reactions of 5-(diethoxyphosphoryl)-1-acyl-2-alkyl(aryl)-2,3-dihydro-4-pyridones
✍ Daniel L Comins; Christian G Ollinger 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 109 KB

Dihydropyridones of the type 1 were converted to their C-5 alkylidene derivatives 2 by a reaction sequence involving phosphorylation, conjugate reduction or addition to provide piperidones 4, and then olefination via a Horner-Wadsworth-Emmons reaction. An intramolecular version of this method was us