- One-pot stereoselective synthesis of 2-acylaziridines and 2-acylpyrrolidines from N-(propargylic)hydroxylamines.
One-pot stereoselective synthesis of 2-acylaziridines and 2-acylpyrrolidines from N-(propargylic)hydroxylamines.
Chemistry, an Asian journal (2013-02-05)
Yoshiaki Miyamoto, Norihiro Wada, Takahiro Soeta, Shuhei Fujinami, Katsuhiko Inomata, Yutaka Ukaji
PMID23377886
ABSTRAKT
The stereoselective direct transformation of N-(propargylic)hydroxylamines into cis-2-acylaziridines was achieved by the combined use of AgBF4 and CuCl. Copper salts were found to promote the transformation of the intermediary 4-isoxazolines into 2-acylaziridines and both 3-aryl- and 3-alkyl-substituted 2-acylaziridines could be prepared by using this method. Furthermore, subsequent 1,3-dipolar cycloaddition of azomethine ylides that were generated in situ from the intermediary 2-acylaziridines with maleimides was achieved in a stereoselective one-pot procedure to afford the corresponding 2-acylpyrrolidines, which consisted of an octahydropyrrolo[3,4-c]pyrrole skeleton.
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