Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks,Organic & Biomolecular Chemistry

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Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-05-22 00:00:00 , DOI: 10.1039/c7ob00832e
Nicola Piens _{1,

2,

3,

4,

5} , Kristof Van Hecke _{4,

5,

6,

7,

8} , Dieter Vogt _{9,

10,

11,

12,

13} , Matthias D'hooghe _{1,

2,

3,

4,

5}

Affiliation

The Co₂(CO)₈-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.

中文翻译：

官能化氮丙啶的羰基钴催化羰基化为通用的β-内酰胺结构单元

研究了具有不同取代模式的不同类别的未活化氮丙啶的Co ₂（CO）₈催化的羰基化作用。特别关注选择性问题和反应优化。这项研究导致了24克新型β-内酰胺靶标结构的立体定位和立体定向合成，高产达数克。通过扩环，闭环和/或侧链官能化方案说明了新获得的氮杂环丁烷-2-酮的合成潜力，从而可以直接进入新型吡咯烷，C稠合的双环和三环β-内酰胺类化合物。和单环碳青霉烯类似物。

更新日期：2017-05-23

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