Stereodivergent Synthesis of β-Lactams Using Thermal Rearrangement of Aminocyclobutenones
作者:Iwao Hachiya、Takuya Yoshitomi、Yukari Yamaguchi、Makoto Shimizu
DOI:10.1021/ol901192y
日期:2009.8.6
In the present study, the stereodivergent synthesis of both cis- and trans-β-lactams is presented using the following three reactions: iminocyclobutenone formation, chemoselective reduction of imino groups, and thermal rearrangement of aminocyclobutenones as crucial steps, in which the starting materials, iminocyclobutenones, were readily synthesized using conjugate addition reactions of alkynyl imines
在本研究中,使用以下三个反应介绍了顺式和反式-β-内酰胺的立体发散性合成:亚氨基环丁烯酮的形成,亚氨基基团的化学选择性还原以及氨基环丁烯酮的热重排等关键步骤,其中原料包括使用炔基亚胺与乙烯酮甲硅烷基乙缩醛的共轭加成反应可以容易地合成亚氨基环丁烯酮,收率很高。