標題: Multicomponent reactions of phosphines, enynedioates and benzylidene malononitriles generated highly substituted cyclopentenes through an unexpected phosphine alpha-addition-delta-evolvement of an anion pathway
作者: Chuang, Shih-Ching
Sung, Shih-Ping
Deng, Jie-Cheng
Chiou, Mong-Feng
Hsu, Day-Shin
應用化學系
Department of Applied Chemistry
公開日期: 2016
摘要: 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.
URI: http://dx.doi.org/10.1039/c5ob02445e
http://hdl.handle.net/11536/133196
ISSN: 1477-0520
DOI: 10.1039/c5ob02445e
期刊: ORGANIC & BIOMOLECULAR CHEMISTRY
Volume: 14
Issue: 7
起始頁: 2306
結束頁: 2317
顯示於類別:期刊論文