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Kinetic Resolution of 2 H ‐Azirines by Asymmetric Imine Amidation
Author(s) -
Hu Haipeng,
Liu Yangbin,
Lin Lili,
Zhang Yuheng,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201605251
Subject(s) - aziridine , imine , kinetic resolution , azirine , chemistry , oxindole , ketone , resolution (logic) , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , ring (chemistry) , artificial intelligence , computer science
Highly efficient kinetic resolution of 2 H ‐azirines by an asymmetric imine amidation was achieved in the presence of a chiral N , N ′‐dioxide/Sc III complex, thus providing a promising method to obtain the enantioenriched 2 H ‐azirine derivatives and protecting‐group free aziridines at the same time. It is rare to find an example of N1 of an oxindole participating in a reaction over C3. Moreover, chiral 2 H ‐azirines were stereospecifically transformed into an unprotected aziridine and α‐amino ketone.
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