dc.contributor.author
Chang, Chenyang
dc.contributor.author
Amos, Stephanie G. E.
dc.contributor.author
Benet-Buchholz, Jordi
dc.contributor.author
Kleij, Arjan W.
dc.date.accessioned
2025-07-03T08:12:01Z
dc.date.available
2025-07-03T08:12:01Z
dc.date.issued
2025-06-12
dc.identifier.uri
http://hdl.handle.net/2072/484494
dc.description.abstract
An effective binary catalytic system enables the synthesis of oxa- and aza-bicyclo[2.2.1]heptanes from cyclic γ-epoxy-alcohols. A combination of an aminotriphenolate Al(III) complex and a bromide salt delivers a wide variety of target compounds in good to excellent yields, with high diastereo-control. The mechanism includes a double-nucleophilic displacement at a carbon center via a proton-relay step involving the Al(III) complex phenolate, as supported by control experiments. Med-chem inspired synthons could successfully be obtained with the aza-bicyclo[2.2.1]heptanes.
ca
dc.publisher
ACS Publications
ca
dc.rights
Attribution-NonCommercial-NoDerivatives 4.0 International
*
dc.rights.uri
http://creativecommons.org/licenses/by-nc-nd/4.0/
*
dc.source
RECERCAT (Dipòsit de la Recerca de Catalunya)
dc.subject.other
Química
ca
dc.title
Proton Relay Catalysis Enables the Synthesis of 2-Oxa- and 2-Azabicyclo[2.2.1]heptanes
ca
dc.type
info:eu-repo/semantics/article
ca
dc.description.version
info:eu-repo/semantics/publishedVersion
ca
dc.relation.projectID
CERCA Program/Generalitat de Catalunya
ca
dc.relation.projectID
MICINN (PID2023-149295NB-I00 and Severo Ochoa Excellence Accreditation 2020–2023 CEX2019-000925-S)
ca
dc.relation.projectID
ICREA
ca
dc.relation.projectID
AGAUR (2021-SGR-00835)
ca
dc.relation.projectID
C.C. thanks the Chinese Research Council for funding of a predoctoral fellowship (2022-06920011)
ca
dc.identifier.doi
https://doi.org/10.1021/acs.orglett.5c01962
ca
dc.rights.accessLevel
info:eu-repo/semantics/openAccess
