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Copper(I)‐Catalyzed [3+1] Cycloaddition of Alkenyldiazoacetates and Iminoiodinanes: Easy Access to Substituted 2‐Azetines
Author(s) -
Barluenga José,
Riesgo Lorena,
Lonzi Giacomo,
Tomás Miguel,
López Luis A.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200998
Subject(s) - cycloaddition , copper , catalysis , chemistry , combinatorial chemistry , materials science , organic chemistry
The copper(I)‐catalyzed reaction of alkenyldiazoacetates and iminoiodinanes affords functionalized azetine derivatives. This process is consistent with the formation of an aziridinyldiazoacetate intermediate, which gives rise to the four‐membered heterocycles by metal‐catalyzed ring expansion. The resulting azetine structure is a direct precursor of azeditine‐2‐carboxylic acid derivatives (EWG=electron‐withdrawing group).