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Multicomponent reactions of phosphines, enynedioates and cinnamaldimines give gamma-lactams with a 1,3,5-hexatriene moiety for facile 6pi electrocyclization: Access to oxindoles, isatins and isoxazolinones
Multicomponent reactions of phosphines, enynedioates and cinnamaldimines generated 3-phosphorus ylide gamma-lactams having a 1,3,5-hexatriene moiety with low activation energy barrier for 6pi electrocyclization, through initial formation of 1,3-dipoles from the alpha(delta’)-Michael addition of phosphines to enynedioates. The reactive 1,3-dipoles underwent addition to cinnamaldimines, lactamization, 6pi electrocyclization and oxidation to give 3-phosphorus ylide oxindoles as platform molecules toward isatins and isoxazolinones. The key step, 6pi electrocyclization, was further examined by a kinetic and a computational study.
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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate