Choi Matthew Kwok-Wai, Yu Wing-Yiu, Che Chi-Ming
Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong.
Org Lett. 2005 Mar 17;7(6):1081-4. doi: 10.1021/ol050003m.
[reaction: see text] An operationally simple catalytic system based on [RuCl(2)(p-cymene)(2)] was developed for stereoselective cyclization of alpha-diazoacetamides by intramolecular carbenoid C-H insertion, and beta-lactams were produced in excellent yields and >99% cis-stereoselectivity. The Ru-catalyzed reactions can be performed without the need for slow addition of diazo compounds and inert atmosphere. With alpha-diazoanilides as substrate, the carbenoid insertion was directed selectively to aromatic C-H bond leading to gamma-lactam formation (>95% yield).
[反应：见正文] 开发了一种基于[RuCl₂(p - 异丙苯)₂]的操作简单的催化体系，用于通过分子内类卡宾C-H插入实现α-重氮乙酰胺的立体选择性环化反应，生成的β-内酰胺产率优异，顺式立体选择性大于99%。钌催化的反应无需缓慢添加重氮化合物，也无需惰性气氛。以α-重氮苯胺为底物时，类卡宾插入反应选择性地导向芳族C-H键，生成γ-内酰胺（产率>95%）。
