title: Multicomponent reactions of phosphines, diynedioates, and aryl aldehydes generated furans appending reactive phosphorus ylides through cumulated trienoates as key intermediates: a phosphine α-addition-δ-evolvement of an anion pathway.
abstract: Multicomponent reactions of phosphines, diynedioates, and aryl aldehydes have been demonstrated, providing trisubstituted furans appending reactive phosphorus ylides, through cumulated trienoates as key intermediates. The proposed trienoate intermediates, 1,5-dipolar species formed via nucleophilic α-attack of phosphines toward diynedioates (α-addition-δ-evolvement of an anion, abbreviated αAδE), undergo addition to aryl aldehydes followed by 5-endo-dig cyclization, proton transfer, and resonance to give trisubstituted furans. Furthermore, the phosphorus ylides are oxidized to α-keto ester furans and utilized as Wittig reagents.
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University , 1001, Ta-Hsueh Road, Hsinchu 30010, Taiwan, R.O.C.
authors.forename: Jie-Cheng
authors.initials: JC
authors.lastname: Deng
authors.forename: Shih-Ching
authors.initials: SC
authors.lastname: Chuang