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Multicomponent Reactions of Phosphines, Enynedioates and Cinnamaldimines Give γ‐Lactams with a 1,3,5‐Hexatriene Moiety for Facile 6π Electrocyclization: Access to Oxindoles, Isatins and Isoxazolinones
Author(s) -
Deng JieCheng,
Chen WuYin,
Zhu Chaoyuan,
Chuang ShihChing
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201401134
Subject(s) - moiety , chemistry , ylide , phosphorus , combinatorial chemistry , organic chemistry
Abstract Multicomponent reactions of phosphines, enynedioates and cinnamaldimines generated 3‐phosphorus ylide γ‐lactams having a 1,3,5‐hexatriene moiety with low activation energy barrier for 6π electrocyclization, through initial formation of 1,3‐dipoles from the α(δ′)‐Michael addition of phosphines to enynedioates. The reactive 1,3‐dipoles underwent addition to cinnamaldimines, lactamization, 6π electrocyclization and oxidation to give 3‐phosphorus ylide oxindoles as platform molecules toward isatins and isoxazolinones. The key step, 6π electrocyclization, was further examined by a kinetic and a computational study.