利用氨基环丁烯酮的热重排进行β-内酰胺的立体发散合成。

Stereodivergent synthesis of beta-lactams using thermal rearrangement of aminocyclobutenones.

作者信息

Hachiya Iwao, Yoshitomi Takuya, Yamaguchi Yukari, Shimizu Makoto

机构信息

Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan.

出版信息

Org Lett. 2009 Aug 6;11(15):3266-8. doi: 10.1021/ol901192y.

DOI:10.1021/ol901192y

PMID:19572744

Abstract

In the present study, the stereodivergent synthesis of both cis- and trans-beta-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 with ketene silyl acetals in good yields.

摘要

在本研究中，通过以下三个反应实现了顺式和反式β-内酰胺的立体发散合成：亚氨基环丁烯酮的形成、亚氨基的化学选择性还原以及氨基环丁烯酮的热重排作为关键步骤，其中起始原料亚氨基环丁烯酮可通过炔基亚胺与烯酮硅基缩醛的共轭加成反应以良好的产率轻松合成。