dc.contributor.author |
Muratore, Michael E. |
dc.contributor.author |
Konovalov, Andrey I. |
dc.contributor.author |
Armengol-Relats, Helena |
dc.contributor.author |
Echavarren, Antonio M. |
dc.date.accessioned |
2019-04-02T13:19:02Z |
dc.date.available |
2019-10-17T02:45:06Z |
dc.date.issued |
2018-10-17 |
dc.identifier.uri |
http://hdl.handle.net/2072/352749 |
dc.format.extent |
15613 p. |
dc.language.iso |
eng |
dc.rights |
L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/ |
dc.source |
RECERCAT (Dipòsit de la Recerca de Catalunya) |
dc.subject.other |
54 |
dc.title |
Diastereospecific Gold(I)-Catalyzed Cyclization Cascade for the Controlled Preparation of N- and N,O-heterocycles |
dc.type |
info:eu-repo/semantics/article |
dc.type |
info:eu-repo/semantics/acceptedVersion |
dc.embargo.terms |
12 mesos |
dc.relation.projectID |
info:eu-repo/grantAgreement/EC/FP7/321066 |
dc.identifier.doi |
10.1002/chem.201802770 |
dc.rights.accessLevel |
info:eu-repo/semantics/openAccess |
dc.description.abstract |
The reaction of oxime-tethered 1,6-enynes with a cationic gold(I) catalyst demonstrates a great potential for the synthesis of a range of heterocycles in a diastereospecific fashion. The control of the configuration of the oxime and the alkene of the enyne moiety is the key to obtain selectively dihydro-1,2-oxazines, isoxazoles or dihydropyrrole-N-oxides as single diastereoisomers. As supported by DFT calculations, these cascade reactions proceed stepwise, by the intramolecular addition of the O or N atom of the oxime onto cyclopropyl gold(I) carbene intermediates. In this study, we have also observed a rare [3,3]-sigmatropic rearrangement of nitrones. |