Piens Nicola, Van Hecke Kristof, Vogt Dieter, D'hooghe Matthias
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Org Biomol Chem. 2017 Jun 7;15(22):4816-4821. doi: 10.1039/c7ob00832e.
The Co(CO)-catalyzed carbonylation of different classes of non-activated aziridines with diverse substitution patterns was investigated. Special attention was devoted to selectivity issues and reaction optimization. This study resulted in the regio- and stereospecific synthesis of 24 novel β-lactam target structures in high yields on a multigram scale. The synthetic potential of the newly obtained azetidin-2-ones was illustrated via ring-expansion, ring-closure, and/or side chain-functionalization protocols to provide a straightforward entry to novel pyrrolidines, C-fused bi- and tricyclic β-lactams and monocyclic carbapenem analogs.
研究了钴（CO）催化的具有不同取代模式的各类非活化氮丙啶的羰基化反应。特别关注了选择性问题和反应优化。该研究以多克规模高产率地实现了24种新型β-内酰胺目标结构的区域和立体特异性合成。通过扩环、环合和/或侧链官能化方案展示了新得到的氮杂环丁烷-2-酮的合成潜力，为新型吡咯烷、碳稠合双环和三环β-内酰胺以及单环碳青霉烯类似物提供了直接的合成途径。
