dc.contributor.author |
Xie, Jianing |
dc.contributor.author |
Li, Xuetong |
dc.contributor.author |
Kleij, Arjan W. |
dc.date.accessioned |
2021-03-17T08:16:50Z |
dc.date.available |
2021-08-06T02:45:06Z |
dc.date.issued |
2020-08-06 |
dc.identifier.uri |
http://hdl.handle.net/2072/445728 |
dc.format.extent |
8839 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 |
Pd-catalyzed stereoselective tandem ring-opening amination/cyclization of vinyl g-lactones: access to caprolactam diversity |
dc.type |
info:eu-repo/semantics/article |
dc.type |
info:eu-repo/semantics/draft |
dc.embargo.terms |
12 mesos |
dc.relation.projectID |
CTQ-2014–60419-R |
dc.relation.projectID |
2017-SGR-232 |
dc.relation.projectID |
2016-06200061 |
dc.relation.projectID |
2019-06870036 |
dc.identifier.doi |
10.1039/d0sc03647a |
dc.rights.accessLevel |
info:eu-repo/semantics/openAccess |
dc.description.abstract |
A stereoselective amination/cyclization cascade process has been developed that allows for the preparation
of a series of unsaturated and substituted caprolactam derivatives in good yields. This conceptually novel
protocol takes advantage of the easy access and modular character of vinyl g-lactones that can be
prepared from simple precursors. Activation of the lactone substrate in the presence of a suitable Pd
precursor and newly developed phosphoramidite ligand offers a stereocontrolled ring-opening/allylic
amination manifold under ambient conditions. The intermediate (E)-configured 3-amino acid can be
cyclized using a suitable dehydrating agent in an efficient one-pot, two-step sequence. This overall
highly chemo-, stereo- and regio-selective transformation streamlines the production of a wide variety
of modifiable and valuable caprolactam building blocks in an operationally attractive way. |