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OBO-Protected Pyruvates as Reagents for the Synthesis of Functionalized Heteroaromatic Compounds

2018; American Chemical Society; Volume: 20; Issue: 13 Linguagem: Inglês

10.1021/acs.orglett.8b01614

1523-7060

Carina Esteves, Maria Koyioni, Kirsten E. Christensen, Peter D. Smith, Timothy J. Donohoe,

Catalytic Cross-Coupling Reactions

Pd-catalyzed α-arylation of methyl-OBO-ketone (OBO = 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl) gives rise to arylated OBO-protected pyruvates. By appropriate prefunctionalization of the aryl ring or by subsequent functionalization at the α-carbonyl position of the arylated OBO-ketones, useful diketo OBO-protected carboxylates can be generated. Cyclization, aromatization, and OBO deprotection of these intermediates, using two distinct routes, gives access to valuable α-acyl heteroaromatic compounds.