DUGiDocsChiral Induction in Intramolecular Rhodium-Catalyzed [2+2+2] Cycloadditions of Optically Active Allene-ene/yne-allene Substrates
dc.contributor.author
dc.date.accessioned
2017-02-02T07:23:50Z
dc.date.available
2017-02-02T07:23:50Z
dc.date.issued
2017-02-02
dc.identifier.issn
1615-4150
dc.identifier.uri
dc.description.abstract
Allene-yne-allene and allene-ene-allene N-tosyl-linked substrates with two chiral centres in the α-position of the allene moiety were satisfactorily prepared starting both from racemic and chiral propargylic alcohols. The Wilkinson's complex-catalyzed [2+2+2] cycloaddition reaction of these substrates was evaluated. In the case of enantiomerically pure bisallenes, high stereoselectivity was observed, giving a diastereomerically pure cycloadduct. The chirality of starting bisallene substrates can be completely transferred to the cycloadducts, representing an atom-economical and enantiospecific process for the construction of fused polycycles. However, when reacting an oxygen-linked allene-ene-allene substrate, the stereoselectivity decreased and two diastereoisomers were formed. A detailed characterization study of the resulting cycloadducts allowed us to identify the enantioisomer generated in the cycloaddition
dc.description.sponsorship
Financial support from the Spanish Ministry of Education and Science (MINECO) (Projects No.: CTQ2014–54306-P, CTQ2015-64436-P and SAF2014-52223-C2-1-R) and the DIUE of the Generalitat de Catalunya (Project No.: 2014SGR931 and predoctoral grant to M.F.) are acknowledged. Thanks are due to UdG for a predoctoral grant to E.H.
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application/pdf
dc.language.iso
eng
dc.publisher
Wiley
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info:eu-repo/grantAgreement/MINECO//CTQ2014-54306-P/ES/ESTUDIOS TEORICO-EXPERIMENTALES DE CICLACIONES CATALIZADAS POR METALES DE TRANSICION. NUEVOS DESARROLLOS EN AROMATICIDAD, FUNCIONALES DE LA DENSIDAD Y QUIMICA SUPRAMOLECULAR/
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Reproducció digital del document publicat a: http://dx.doi.org/10.1002/adsc.201600613
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© Advanced Synthesis and Catalysis, 2016, vol. 359, núm. 3, p. 506-512
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Articles publicats (D-Q)
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Tots els drets reservats
dc.title
Chiral Induction in Intramolecular Rhodium-Catalyzed [2+2+2] Cycloadditions of Optically Active Allene-ene/yne-allene Substrates
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/embargoedAccess
dc.embargo.terms
Cap
dc.date.embargoEndDate
info:eu-repo/date/embargoEnd/2026-01-01
dc.type.version
info:eu-repo/semantics/publishedVersion
dc.identifier.doi
dc.identifier.idgrec
026074
dc.contributor.funder
dc.relation.ProjectAcronym
dc.identifier.eissn
1615-4169