Diamidocarbenes as versatile and reversible [2+1] cycloaddition reagents
Cited 42 times inCited 41 times in
- Diamidocarbenes as versatile and reversible [2+1] cycloaddition reagents
- Moerdyk, Jonathan P.; Bielawski, Christopher W.
- Issue Date
- NATURE PUBLISHING GROUP
- NATURE CHEMISTRY, v.4, no.4, pp.275 - 280
- We describe the synthesis of a variety of cyclopropanes and epoxides by combining a readily accessible and isolable N,N-2-diamidocarbene with a range of structurally and electronically diverse olefins and aldehydes, including electron-rich derivatives. Surprisingly, the cyclopropanation and epoxidation reactions were discovered to be rapid and thermally reversible at relatively low temperatures, two features often desired for applications that utilize dynamic covalent chemistry. In addition, a diamidocyclopropane derivative prepared via this method was hydrolysed successfully to form the corresponding linear carboxylic acid in a metal-and carbon monoxide-free hydrocarboxylation reaction. As such, diamidocarbenes are expected to find utility in the synthesis of cyclopropanes, epoxides and their derivatives, as well as in dynamic covalent chemistry applications.
- Appears in Collections:
- CHM_Journal Papers
- Files in This Item:
- There are no files associated with this item.
can give you direct access to the published full text of this article. (UNISTARs only)
Show full item record
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.