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Abstract
Recent syntheses of azetidines, pyrrolidines, piperidines and azepines through cycloaddition or sigmatropic rearrangements of vinylaziridines are described. Applications to natural product synthesis and mechanistic investigations are also summarized.
Highlights
Vinylaziridines, which simultaneously possesses electrophilic and nucleophilic centers in their structure, have been regarded as highly valuable synthetic intermediates because of their unique reactivity toward various other reactive species such as activated alkenes, heteroatoms and metallic species [1]
In the early 2000s, a silyl-substituted vinylaziridine was converted into a 6-membered azacycle under similar reaction conditions (Equation 2 in Scheme 2) [5]
Most recent pyrrolidine syntheses from vinylaziridines apply transition metal catalysts, especially
Summary
Vinylaziridines, which simultaneously possesses electrophilic and nucleophilic centers in their structure, have been regarded as highly valuable synthetic intermediates because of their unique reactivity toward various other reactive species such as activated alkenes, heteroatoms and metallic species [1]. Nowadays the vinylaziridine moiety plays an important role in the preparation of 4-, 5-, 6- and 7-membered azacycles according to the selection of reagents and reaction conditions (Scheme 1). Because this transformation releases the severe ring strain of the aziridine ring, this conversion usually proceeds in a highly efficient manner. In light of this unique reactivity and effectiveness, a lot of synthetic research in this area is being carried out even now.
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