1,5-Stereoinduction in Boron-Mediated Aldol Reactions of beta,delta-Bisalkoxy Methylketones Containing Cyclic Protecting Groups

dc.creatorDias, LC
dc.creatorPolo, EC
dc.creatorFerreira, MAB
dc.creatorTormena, CF
dc.date2012
dc.dateAPR 20
dc.date2014-07-30T13:38:41Z
dc.date2015-11-26T17:47:46Z
dc.date2014-07-30T13:38:41Z
dc.date2015-11-26T17:47:46Z
dc.date.accessioned2018-03-29T00:30:30Z
dc.date.available2018-03-29T00:30:30Z
dc.identifierJournal Of Organic Chemistry. Amer Chemical Soc, v. 77, n. 8, n. 3766, n. 3792, 2012.
dc.identifier0022-3263
dc.identifierWOS:000302982000008
dc.identifier10.1021/jo300125d
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/52504
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/52504
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1288886
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionA study of the aldol reactions of boron enolates from methylketones that are protected with dimethylacetonide or di-tert-butylsilyl groups and that possess a trans or cis relationship between the chiral centers is presented. The main objective of this work was to evaluate the influence of the relative stereochemistry between the chiral centers and the steric and electronic influences of the cyclic protecting groups on the aldol reactions. The aldol adducts were obtained with moderate to high 1,5-anti stereoselectivity that was dependent on both the identity of the protecting group on the beta,delta-oxygen stereocenters and the relative stereochemistry between the beta and delta chiral centers. A theoretical analysis of the transition states involving these aldol reactions was performed utilizing DFT (density functional theory).
dc.description77
dc.description8
dc.description3766
dc.description3792
dc.descriptionFAEP-UNICAMP
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCNPq [Proc. CNPq 573.564/2008-6]
dc.languageen
dc.publisherAmer Chemical Soc
dc.publisherWashington
dc.publisherEUA
dc.relationJournal Of Organic Chemistry
dc.relationJ. Org. Chem.
dc.rightsfechado
dc.sourceWeb of Science
dc.subjectOxygenated Methyl Ketones
dc.subjectBeta-alkoxy Methylketones
dc.subjectUniversal Nmr Database
dc.subject1,5-asymmetric Induction
dc.subjectAddition-reactions
dc.subjectStereochemical Assignment
dc.subject1,5-anti Stereoinduction
dc.subjectAsymmetric-synthesis
dc.subject1,3-diol Acetonides
dc.subjectDirected Reduction
dc.title1,5-Stereoinduction in Boron-Mediated Aldol Reactions of beta,delta-Bisalkoxy Methylketones Containing Cyclic Protecting Groups
dc.typeArtículos de revistas


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