Ferreira Juliana, Duarte Vera C M, Noro Jennifer, Gil Fortes António, Alves Maria J
Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal.
Org Biomol Chem. 2016 Mar 14;14(10):2930-7. doi: 10.1039/c5ob02594j.
Different electron-rich dienophiles were combined with the imine obtained from 2,4-O-benzylidene-d-erythrose and p-anisidine furnishing enantiomerically pure tetrahydroquinolines, by inverse electron-demand [4π + 2π] cycloaddition. The imine was also reacted with 2-substituted electron-rich 1,3-butadienes giving the diastereomeric pure product, resulting from the normal electron demand cycloaddition. The facial selectivity of both processes is proposed on the basis of a 1,4-relationship between the hydroxyl group and the nitrogen atom in the chiral N-(p-methoxyphenyl)imine derivative.
通过逆电子需求的[4π + 2π]环加成反应，将不同的富电子亲双烯体与由2,4-O-亚苄基-d-赤藓糖和对甲氧基苯胺得到的亚胺相结合，得到对映体纯的四氢喹啉。该亚胺还与2-取代的富电子1,3-丁二烯反应，通过正常电子需求的环加成反应得到非对映体纯的产物。基于手性N-(对甲氧基苯基)亚胺衍生物中羟基与氮原子之间的1,4-关系，提出了这两个过程的面选择性。
