Moreno-Clavijo Elena, Carmona Ana T, Reissig Hans-Ulrich, Moreno-Vargas Antonio J, Alvarez Eleuterio, Robina Inmaculada
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, 1, E-41012 Seville, Spain.
Org Lett. 2009 Nov 5;11(21):4778-81. doi: 10.1021/ol902097d.
Efficient methodologies for the synthesis of regioisomeric 3-pyrrolines by reaction of electron-deficient imines and sulfur-containing allenyl derivatives are presented. Lithiated thioallenes give 2-aryl-3-phenylsulfonyl-3-pyrrolines, whereas allenyl sulfones furnish the isomeric 2-aryl-4-phenylsulfonyl-3-pyrrolines through migration of the sulfonyl group that catalyzes the nucleophilic [3 + 2] cycloaddition.
本文介绍了通过缺电子亚胺与含硫烯丙基衍生物反应合成区域异构体3-吡咯啉的有效方法。锂化硫代丙二烯生成2-芳基-3-苯基磺酰基-3-吡咯啉,而烯丙基砜则通过催化亲核[3+2]环加成的磺酰基迁移生成异构体2-芳基-4-苯基磺酰基-3-吡咯啉。