Organocatalytic Nucleophilic Ring Opening of Cyclopropanecarbaldehydes by Benzenethiols: Tandem Synthesis of Benzo[b]thiepines
作者:Quanrui Wang、Liangxi Li、Zhiming Li
DOI:10.1055/s-0029-1217370
日期:2009.7
An unprecedented nucleophilic ring opening of cyclopropanecarbaldehydes with benzenethiols proceeds regioselectively under the catalysis of 40 mol% proline to afford fair to good yields of 4-phenylthio-substituted butyraldehydes. If o-thiosalicyl-aldehydes are employed, a tandem homoconjugate addition―aldol reaction occurs, which constitutes an expedient entry to pharmaceutically valuable 2,3-dihy
环丙烷甲醛与苯硫醇的前所未有的亲核开环在 40 mol% 脯氨酸的催化下区域选择性地进行,以提供公平到良好的 4-苯硫基取代丁醛收率。如果使用邻硫代水杨醛,会发生串联的共轭加成 - 羟醛反应,这构成了进入具有药用价值的 2,3-二氢苯并[b] 噻平-4-甲醛的有利入口。