Substrate and catalyst effects in C-H insertion reactions of α-diazoacetamides
| dc.contributor.author | Ring, Aoife | |
| dc.contributor.author | Ford, Alan | |
| dc.contributor.author | Maguire, Anita R. | |
| dc.contributor.funder | Higher Education Authority | en |
| dc.contributor.funder | Cork County Council | en |
| dc.date.accessioned | 2016-11-01T14:57:43Z | |
| dc.date.available | 2016-11-01T14:57:43Z | |
| dc.date.issued | 2016-10-22 | |
| dc.date.updated | 2016-11-01T14:49:11Z | |
| dc.description.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. | en |
| dc.description.sponsorship | Higher Education Authority (Programme for Research in Third Level Institutions Cycle 4) | en |
| dc.description.status | Peer reviewed | en |
| dc.description.version | Accepted Version | en |
| dc.format.mimetype | application/pdf | en |
| dc.identifier.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. | en |
| dc.identifier.doi | 10.1016/j.tetlet.2016.10.081 | |
| dc.identifier.endpage | 5406 | |
| dc.identifier.issn | 0040-4039 | |
| dc.identifier.journaltitle | Tetrahedron Letters | en |
| dc.identifier.startpage | 5399 | |
| dc.identifier.uri | https://hdl.handle.net/10468/3230 | |
| dc.identifier.volume | 57 | |
| dc.language.iso | en | en |
| dc.publisher | Elsevier | en |
| dc.relation.uri | http://www.sciencedirect.com/science/article/pii/S0040403916314010 | |
| dc.rights | © 2016, Elsevier. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ | en |
| dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | en |
| dc.subject | C-H insertion | en |
| dc.subject | Diazoacetamides | en |
| dc.subject | Catalyst effects | en |
| dc.subject | Gamma-lactams | en |
| dc.subject | ß-lactams | en |
| dc.title | Substrate and catalyst effects in C-H insertion reactions of α-diazoacetamides | en |
| dc.type | Article (peer-reviewed) | en |
