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 |