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One‐Pot Stereoselective Synthesis of 2‐Acylaziridines and 2‐Acylpyrrolidines from N ‐(Propargylic)hydroxylamines
Author(s) -
Miyamoto Yoshiaki,
Wada Norihiro,
Soeta Takahiro,
Fujinami Shuhei,
Inomata Katsuhiko,
Ukaji Yutaka
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201201180
Subject(s) - stereoselectivity , chemistry , cycloaddition , alkyl , transformation (genetics) , 1,3 dipolar cycloaddition , aryl , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , gene
The stereoselective direct transformation of N ‐(propargylic)hydroxylamines into cis ‐2‐acylaziridines was achieved by the combined use of AgBF 4 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.