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Type: Artigo de periódico
Title: Intermolecular Enantioselective Heck-matsuda Arylations Of Acyclic Olefins: Application To The Synthesis Of β-aryl-γ-lactones And β-aryl Aldehydes.
Author: Oliveira, Caio C
Angnes, Ricardo A
Correia, Carlos Roque D
Abstract: We 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.
Citation: The Journal Of Organic Chemistry. v. 78, n. 9, p. 4373-85, 2013-May.
Rights: fechado
Identifier DOI: 10.1021/jo400378g
Date Issue: 2013
Appears in Collections:Unicamp - Artigos e Outros Documentos

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