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Direct and Stereospecific Synthesis of N ‐H and N ‐Alkyl Aziridines from Unactivated Olefins Using Hydroxylamine‐ O ‐Sulfonic Acids
Author(s) -
Ma Zhiwei,
Zhou Zhe,
Kürti László
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705530
Subject(s) - hydroxylamine , stereospecificity , chemistry , alkyl , reagent , sulfonic acid , functional group , organic chemistry , nitro , medicinal chemistry , catalysis , polymer
A Rh II ‐catalyzed direct and stereospecific N ‐H‐ and N ‐alkyl aziridination of olefins is reported that uses hydroxylamine‐ O ‐sulfonic acids as inexpensive, readily available, and nitro group‐free aminating reagents. Unactivated olefins, featuring a wide range of functional groups, are converted into the corresponding N ‐H or N ‐alkyl aziridines in good to excellent yields. This operationally simple, scalable transformation proceeds efficiently at ambient temperature and is tolerant towards oxygen and trace moisture.