Intermolecular Enantioselective Heck-matsuda Arylations Of Acyclic Olefins: Application To The Synthesis Of β-aryl-γ-lactones And β-aryl Aldehydes.

dc.creatorOliveira, Caio C
dc.creatorAngnes, Ricardo A
dc.creatorCorreia, Carlos Roque D
dc.date2013-May
dc.date2015-11-27T13:31:36Z
dc.date2015-11-27T13:31:36Z
dc.date.accessioned2018-03-29T01:17:35Z
dc.date.available2018-03-29T01:17:35Z
dc.identifierThe Journal Of Organic Chemistry. v. 78, n. 9, p. 4373-85, 2013-May.
dc.identifier1520-6904
dc.identifier10.1021/jo400378g
dc.identifierhttp://www.ncbi.nlm.nih.gov/pubmed/23570395
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/200581
dc.identifier23570395
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1300814
dc.descriptionWe describe herein a synthetically useful method for the enantioselective intermolecular Heck-Matsuda arylation of acyclic allylic alcohols. Aryldiazonium tetrafluoroborates were applied as arylating agents in the presence of Pd(TFA)2 and a chiral, commercially available, bisoxazoline ligand. The methodology is straightforward, robust, scalable up to a few grams, and of broad scope allowing the synthesis of a range of β-aryl-carbonyl compounds in good to high enantioselectivities and yields. This new enantioselective Heck-Matsuda arylation allowed the synthesis of β-aryl-γ-lactones and β-aryl aldehydes, which play a vital role as key intermediates in the synthesis of the biologically active compounds, such as (R)-baclofen, (R)-rolipram, (S)-curcumene, (S)-dehydrocurcumene, and (S)-tumerone.
dc.description78
dc.description4373-85
dc.languageeng
dc.relationThe Journal Of Organic Chemistry
dc.relationJ. Org. Chem.
dc.rightsfechado
dc.rights
dc.sourcePubMed
dc.titleIntermolecular Enantioselective Heck-matsuda Arylations Of Acyclic Olefins: Application To The Synthesis Of β-aryl-γ-lactones And β-aryl Aldehydes.
dc.typeArtículos de revistas


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