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...
Saved in:
Published in | Journal of organic chemistry Vol. 83; no. 19; pp. 12255 - 12260 |
---|---|
Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
05.10.2018
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
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. |
---|---|
Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.8b01673 |