Copper-catalyzed asymmetric oxidation of sulfides
| dc.contributor.author | O'Mahony, Graham E. | |
| dc.contributor.author | Ford, Alan | |
| dc.contributor.author | Maguire, Anita R. | |
| dc.contributor.funder | Irish Research Council for Science Engineering and Technology | en |
| dc.date.accessioned | 2013-02-26T09:57:54Z | |
| dc.date.available | 2013-02-26T09:57:54Z | |
| dc.date.issued | 2012-02-24 | |
| dc.description.abstract | Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence of variation of solvent and ligand structure was examined, and the optimized conditions were then used to oxidize a number of aryl alkyl and aryl benzyl sulfides, producing sulfoxides in excellent yields in most cases (up to 92%), and good enantiopurities in certain cases (up to 84% ee). | en |
| dc.description.sponsorship | IRCSET (EMBARK Initiative) | en |
| dc.description.status | Peer reviewed | en |
| dc.description.version | Accepted Version | en |
| dc.format.mimetype | application/pdf | en |
| dc.identifier.citation | O’MAHONY, G. E., FORD, A. & MAGUIRE, A. R. 2012. Copper-Catalyzed Asymmetric Oxidation of Sulfides. Journal of organic chemistry, 77 (7), 3288-3296. doi: 10.1021/jo2026178 | en |
| dc.identifier.doi | 10.1021/jo2026178 | |
| dc.identifier.endpage | 3296 | en |
| dc.identifier.issued | 7 | en |
| dc.identifier.journaltitle | Journal of Organic Chemistry | en |
| dc.identifier.startpage | 3288 | en |
| dc.identifier.uri | https://hdl.handle.net/10468/988 | |
| dc.identifier.volume | 77 | en |
| dc.language.iso | en | en |
| dc.publisher | ACS Publications | en |
| dc.relation.uri | http://pubs.acs.org/doi/abs/10.1021/jo2026178 | |
| dc.rights | © 2011, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher.To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/jo2026178 | en |
| dc.subject | Copper-catalyzed | en |
| dc.subject | Asymmetric | en |
| dc.subject | Oxidation | en |
| dc.subject | Sulfides | en |
| dc.subject | Sulfoxidation | en |
| dc.title | Copper-catalyzed asymmetric oxidation of sulfides | en |
| dc.type | Article (peer-reviewed) | en |
