Title: Multicomponent Reactions of Phosphines, Enynedioates and Cinnamaldimines Give gamma-Lactams with a 1,3,5-Hexatriene Moiety for Facile 6 pi Electrocyclization: Access to Oxindoles, Isatins and Isoxazolinones
Authors: Deng, Jie-Cheng
Chen, Wu-Yin
Zhu, Chaoyuan
Chuang, Shih-Ching
Department of Applied Chemistry
Keywords: electrocyclic reactions;Michael addition;multicomponent reactions;phosphorus;transition states
Issue Date: 4-May-2015
Abstract: 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 6 pi 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, 6 pi electrocyclization and oxidation to give 3-phosphorus ylide oxindoles as platform molecules toward isatins and isoxazolinones. The key step, 6 pi electrocyclization, was further examined by a kinetic and a computational study.
URI: http://dx.doi.org/10.1002/adsc.201401134
ISSN: 1615-4150
DOI: 10.1002/adsc.201401134
Volume: 357
Begin Page: 1453
End Page: 1462
Appears in Collections:Articles