Access to this article is restricted until 24 months after publication by the request of the publisher.. Restriction lift date: 2018-10-22
Substrate and catalyst effects in C-H insertion reactions of α-diazoacetamides
Loading...
Files
Accepted Version
Date
2016-10-22
Authors
Ring, Aoife
Ford, Alan
Maguire, Anita R.
Journal Title
Journal ISSN
Volume Title
Publisher
Elsevier
Published Version
Abstract
Intramolecular C–H insertion reactions of α-diazocarbonyl compounds typically proceed with preferential five-membered ring formation. However, the presence of a heteroatom such as nitrogen can activate an adjacent C–H site toward insertion resulting in regiocontrol issues. In the case of α-diazoacetamide derivatives, both β- and γ-lactam products are possible owing to this activating effect. Both β- and γ-lactam products are powerful synthetic building blocks in the area of organic synthesis, as well as a common scaffold in a range of natural and pharmaceutical products and therefore C–H insertion reactions to form such compounds are attractive processes.
Description
Keywords
C-H insertion , Diazoacetamides , Catalyst effects , Gamma-lactams , ß-lactams
Citation
Ring, A., Ford, A. and Maguire, A. R. (2016) 'Substrate and catalyst effects in C–H insertion reactions of α-diazoacetamides', Tetrahedron Letters, 57(49), pp. 5399-5406.