Direct N‑H/N‑Me Aziridination of Unactivated Olefins Using O‑(Sulfonyl)hydroxylamines as Aminating Agents

Unactivated aziridines are the core substructures in a plethora of bioactive natural products and serve as building blocks in organic synthesis. Despite this, very limited methods are available to access them directly from olefins, as most of the known methods are devoted to their activated counterp...

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Published inJournal of organic chemistry Vol. 83; no. 19; pp. 12255 - 12260
Main Authors Sabir, Shekh, Pandey, Chandra Bhan, Yadav, Ajay K, Tiwari, Bhoopendra, Jat, Jawahar L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.10.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
H-AZIRIDINES
FUNCTIONALIZATION
HETEROCYCLES
NONACTIVATED AZIRIDINES
REACTIVITY
CHEMISTRY
STEREOSPECIFIC SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
UNPROTECTED AZIRIDINES
SUBSTITUTED AZIRIDINES
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Summary:Unactivated aziridines are the core substructures in a plethora of bioactive natural products and serve as building blocks in organic synthesis. Despite this, very limited methods are available to access them directly from olefins, as most of the known methods are devoted to their activated counterparts. Herein, we have developed a highly efficient Rh­(II)-catalyzed method for the direct preparation of unactivated aziridines from olefins using O-(sulfonyl)­hydroxylamines as the aminating agent. The reactions proceed with a high stereospecificity.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01673