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dc.contributor.authorInfante Blanco, Rebeca
dc.contributor.authorNieto Román, Francisco Javier 
dc.contributor.authorAndrés Juan, Celia 
dc.date.accessioned2016-12-05T13:05:23Z
dc.date.available2016-12-05T13:05:23Z
dc.date.issued2014
dc.identifier.citationOrganic & Biomolecular Chemistry, 2014, 12, p. 345-354es
dc.identifier.issn1477-0520es
dc.identifier.urihttp://uvadoc.uva.es/handle/10324/21449
dc.descriptionProducción Científicaes
dc.description.abstractThe enantio‐ and diastereoselective one‐pot ethylation/cyclopropanation is efficiently promoted by a chiral perhydrobenzoxazine. The catalytic system tolerates a wide range of di‐ and trisubstituted α,β‐unsaturated aldehydes and has been found to be highly diastereo- and enantioselective. Enals leading to intermediates lacking allylic strain or with either A1,2 or A1,3 strain afford the corresponding syn hydroxycyclopropanes very selectively. While α‐methyl enals are successfully ethylated/cyclopropanated, the presence of bulky substituents at alpha position of the enal constitutes a limitation to the substrate scope. The use of 1,1‐diiodoethane allows the obtention of the corresponding enantioenriched cyclopropylcarbinol, which bears carbon‐substituents at all three positions of the ring, with good enantiocontrol, although moderate diastereoselectivity. A procedure for the asymmetric one‐pot arylation/cyclopropanation of enals is proposed, which involves the use of triarylboroxin, diethylzinc and diiodomethane.es
dc.format.mimetypeapplication/pdfes
dc.language.isoenges
dc.publisherRoyal Society of Chemistryes
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectQuímica orgánicaes
dc.titleTandem Diastereo- and Enantioselective Preparation of Aryl and Alkyl Cyclopropyl Carbinols with Three Adjacent Stereocenters Using Perhydrobenzoxazines and Diethylzinces
dc.typeinfo:eu-repo/semantics/articlees
dc.identifier.doi10.1039/C3OB41797Bes
dc.relation.publisherversionhttp://pubs.rsc.org/es
dc.identifier.publicationfirstpage345es
dc.identifier.publicationissue12es
dc.identifier.publicationlastpage354es
dc.identifier.publicationtitleOrganic & Biomolecular Chemistryes
dc.peerreviewedSIes
dc.description.projectMinisterio de Economía, Industria y Competitividad (CTQ 2011-28487)es
dc.description.projectJunta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)es
dc.description.projectUniversidad de Valladolid for a pre-doctoral fellowshipses
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International


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