title: Multicomponent reactions of phosphines, enynedioates and benzylidene malononitriles generated highly substituted cyclopentenes through an unexpected phosphine α-addition-δ-evolvement of an anion pathway.
abstract: Multicomponent reactions of phosphines, enynedioates and benzylidene malononitriles provide highly substituted syn-selective cyclopentenes appending the phosphorus ylide moiety in good yield with a diastereoselectivity of up to 100% through resonance-derived 1,5-dipolar species as the key intermediates, via the nucleophilic α(δ')-attack of phosphines toward enynedioates followed by addition to benzylidene malononitriles and 5-exo-dig cyclization. Through computational analyses, the overall reactions for the formation of syn- and anti-diastereomers are both exothermic with 65.6 and 66.3 kcal mol(-1) at the B3LYP-D3/6-31G(d) level of theory and were found to be kinetically controlled, which favours the formation of syn-diastereomers.
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan, Republic of China. jscchuang@faculty.nctu.edu.tw.
authors.forename: Shih-Ching
authors.initials: SC
authors.lastname: Chuang
authors.forename: Shih-Ping
authors.initials: SP
authors.lastname: Sung
authors.forename: Jie-Cheng
authors.initials: JC
authors.lastname: Deng
authors.forename: Mong-Feng
authors.initials: MF
authors.lastname: Chiou
authors.forename: Day-Shin
authors.initials: DS
authors.lastname: Hsu