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Carbonylation of Aziridines as a Powerful Tool for the Synthesis of Functionalized β‐Lactams
Author(s) -
Piens Nicola,
D'hooghe Matthias
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700698
Subject(s) - carbonylation , aziridine , chemistry , rhodium , palladium , catalysis , combinatorial chemistry , chemical transformation , transition metal , carbon monoxide , organic chemistry , ring (chemistry)
Within heterocyclic chemistry, β‐lactams comprise an extraordinary class of strained compounds, recognized for their biological importance as potent antibiotics and their chemical value as flexible building blocks for the construction of diverse nitrogen‐containing structures. Among the synthetic routes available to access this interesting scaffold, the carbonylation of aziridines, in which carbon monoxide is inserted into one of the ring carbon–nitrogen bonds, is praised for its efficiency and remarkable regio‐ and stereoselectivity. This review provides a comprehensive overview of aziridine‐to‐azetidin‐2‐one carbonylation studies. The protocols are categorized according to the different transition metals (i.e. rhodium, palladium, nickel, iron, and cobalt) that have been employed (in a catalytic or stoichiometric amount) to effect this transformation.