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|Type:||Artigo de periódico|
|Title:||Intermolecular Enantioselective Heck-Matsuda Arylations of Acyclic Olefins: Application to the Synthesis of beta-Aryl-gamma-lactones and beta-Aryl Aldehydes|
|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 beta-aryl-carbonyl compounds in good to high enantioselectivities and yields. This new enantioselective Heck-Matsuda arylation allowed the synthesis of beta-aryl-gamma-lactones and beta-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.|
|Editor:||Amer Chemical Soc|
|Citation:||Journal Of Organic Chemistry. Amer Chemical Soc, v. 78, n. 9, n. 4373, n. 4385, 2013.|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
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