An intramolecular journey of a carboxyl group around 1,2-dihydropyridines: multisite delta- versus gamma-lactonization reactions

作者：Parlier Andree; Kadouri Puchot Catherine; Beaupierre Sandra; Jarosz Nathalie; Rudler Henri^*; Hamon Louis; Herson Patrick; Daran Jean Claude

来源：Tetrahedron Letters, 2009, 50(52): 7274-7279.

DOI：10.1016/j.tetlet.2009.10.038

• 1,2-Dihydropyridines
• Lactones
• Ring-closing/ring-opening
• Rearrangements
• Synthetic methods

In contrast to substituted 4-acetic acid 1,4-dihydropyridines, giving only 6-lactones upon intramolecular reactions, 2-substituted 1,2-dihydropyridines led, besides to 8-lactones, also to new, structurally interesting gamma-lactones as the result of a bromine-induced carbon-carbon double bond 'Umpolung'.