DUGiDocsRhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
dc.contributor.author
dc.date.accessioned
2016-11-16T11:24:34Z
dc.date.available
2016-11-16T11:24:34Z
dc.date.issued
2016-06-02
dc.identifier.issn
1615-4150
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dc.description.abstract
A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respectively) were obtained with complete diastereoselectivity and high enantioselectivity (84-97%) through a kinetic resolution of the M-B-H adduct. Furthermore, these highly substituted cyclohexadienes reacted with dienophiles to afford the corresponding Diels-Alder cycloadducts in good yields
dc.description.sponsorship
Financial support from the Spanish Ministry of Education and Science (MINECO) (Projects No.: CTQ2014-54306-P, CTQ2012-32436 and a RyC contract to A. L.) and the DIUE of the Generalitat de Catalunya (Project No.: 2014SGR931) are acknowledged
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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/
AGAUR/2014-2016/2014 SGR-931
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Versió postprint del document publicat a: http://dx.doi.org/10.1002/adsc.201600039
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© Advanced Synthesis and Catalysis, 2016, vol. 358, núm. 11, p. 1848-1853
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Articles publicats (D-Q)
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Tots els drets reservats
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dc.title
Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/openAccess
dc.embargo.terms
Cap
dc.type.version
info:eu-repo/semantics/acceptedVersion
dc.identifier.doi
dc.identifier.idgrec
025079
dc.contributor.funder
dc.type.peerreviewed
peer-reviewed
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dc.identifier.eissn
1615-4169