Multicomponent reactions of phosphines, enynedioates and benzylidene malononitriles generated highly substituted cyclopentenes through an unexpected phosphine α-addition-δ-evolvement of an anion pathway
| Autor: | Shih-Ping Sung, Shih-Ching Chuang, Jie-Cheng Deng, Day-Shin Hsu, Mong-Feng Chiou |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Stereochemistry Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Ion chemistry.chemical_compound chemistry Nucleophile Ylide Yield (chemistry) Moiety Physical and Theoretical Chemistry Phosphine |
| Zdroj: | Organic & Biomolecular Chemistry. 14:2306-2317 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c5ob02445e |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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