Intramolecular Arylation of Tertiary Enamides through Pd(OAc)2-Catalyzed Dehydrogenative Cross-Coupling Reaction: Construction of Fused N-Heterocyclic Scaffolds and Synthesis of Isoindolobenzazepine Alkaloids

Zhu, WenjuTong, ShuoZhu, JiepingWang, Mei-Xiang2019-04-252019-04-252019-04-25201910.1021/acs.joc.9b00010https://infoscience.epfl.ch/handle/20.500.14299/156123Pd(OAc)2-catalyzed intramolecular dehydrogenative cross-coupling reaction between tertiary enamides, which were derived from the condensation of 2-arylethylamines and methyl o-acetylbenzoate, and arenes enabled synthesis of 7,8-dihydro-5H-benzo[4,5]azepino[2,1-a]-isoindol-5-one derivatives under mild conditions. The synthetic method was applied in the total synthesis of aporhoeadane alkaloids palmanine, lennoxamine, and chilenamine in only three or four steps.Intramolecular Arylation of Tertiary Enamides through Pd(OAc)2-Catalyzed Dehydrogenative Cross-Coupling Reaction: Construction of Fused N-Heterocyclic Scaffolds and Synthesis of Isoindolobenzazepine Alkaloidstext::journal::journal article::research article