Browsing by Author "Sung, Shih-Ping"

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Highly diastereoselective synthesis of substituted cyclopentenes through multicomponent reactions of phosphines, enynedioates, and benzylidene malononitriles via an unexpected phosphine alpha-addition-delta-evolvement of an anion pathway
(2016-03-13)
Chuang, Shih-Ching
;
Sung, Shih-Ping
;
應用化學系
;
Department of Applied Chemistry
Multicomponent reactions of phosphines, enynedioates and benzylidene malononitriles generated highly substituted cyclopentenes through an unexpected phosphine alpha-addition-delta-evolvement of an anion pathway
(2016)
Chuang, Shih-Ching
;
Sung, Shih-Ping
;
Deng, Jie-Cheng
;
Chiou, Mong-Feng
;
Hsu, Day-Shin
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 alpha(delta\')-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.