title: Intermolecular enantioselective Heck-Matsuda arylations of acyclic olefins: application to the synthesis of β-aryl-γ-lactones and β-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 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.
authors.affiliation: Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, CEP. 13083-970, Campinas, São Paulo, Brazil.
authors.forename: Caio C
authors.initials: CC
authors.lastname: Oliveira
authors.forename: Ricardo A
authors.initials: RA
authors.lastname: Angnes
authors.forename: Carlos Roque D
authors.initials: CR
authors.lastname: Correia