Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks

Organic & Biomolecular Chemistry
Nicola PiensMatthias D'hooghe

Abstract

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.

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Citations

Oct 13, 2017·Chemistry : a European Journal·Nicola PiensMatthias D'hooghe
Sep 14, 2018·Organic & Biomolecular Chemistry·Seyedmorteza Hosseyni, Aliasghar Jarrahpour
Aug 28, 2020·Acta Crystallographica. Section E, Crystallographic Communications·Brendan TwamleyMary J Meegan

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