Schurgers Ben, Brigou Ben, Urbanczyk-Lipkowska Zofia, Tourwé Dirk, Ballet Steven, De Proft Frank, Van Lommen Guy, Verniest Guido
Research Group of Organic Chemistry, Department of Chemistry and Department of Bio-engineering Sciences, Faculty of Science and Bio-engineering Sciences and ‡Department of General Chemistry, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.
Org Lett. 2014 Jul 18;16(14):3712-5. doi: 10.1021/ol501529z. Epub 2014 Jul 9.
Novel tricyclic tetrahydroazepinones were synthesized via an in situ Diels-Alder reaction of furan with cyclic allenamides. These reactive intermediates are the first examples of cyclic seven-membered allenamides and were prepared starting from N-(2-chloroallyl)-2-allylglycine derivatives via ring-closing metathesis followed by dehydrochlorination. The trapping of the intermediate cycloallene with furan occurred endo- and regioselectively and provided a convenient entry into new building blocks for medicinal chemistry. The diastereoselectivity of the cycloaddition was confirmed using quantum chemical computations.
通过呋喃与环状烯丙酰胺的原位狄尔斯-阿尔德反应合成了新型三环四氢氮杂卓酮。这些反应性中间体是环状七元烯丙酰胺的首例,它们是从N-(2-氯烯丙基)-2-烯丙基甘氨酸衍生物开始,通过闭环复分解反应然后脱氯化氢制备的。呋喃对中间体环丙二烯的捕获具有内型和区域选择性,为药物化学新结构单元的构建提供了便利途径。利用量子化学计算证实了环加成反应的非对映选择性。