Decarboxylation-promoted Pd-catalyzed asymmetric propargylic [3 + 2] annulation for the enantioselective construction of a quaternary stereocenter in 2,3-dihydrofurans
Organic & Biomolecular Chemistry(2018)
Abstract
The enantioselective construction of a quaternary stereocenter in 2,3-dihydrofuran frameworks has been realized via the palladium-catalyzed asymmetric [3 + 2] cycloaddition of tertiary propargylic carbonates with beta-ketoesters enabled by a chiral ferrocene/benzimidazole-based bidentate P, N-ligand. The reaction was significantly promoted by loss of CO2 to irreversibly form p-propargylpalladium or allenylpalladium intermediates. This protocol features a good tolerance of functional groups in both tertiary propargylic carbonates and beta-ketoesters, thereby delivering a variety of highly functionalized chiral 2,3-dihydrofurans bearing a quaternary stereocenter at the 2-position and an exocyclic double bond at the 3-position in good chemical yields and high enantioselectivities (up to 98% ee).
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Key words
enantioselective construction,quaternary stereocenter,decarboxylation-promoted,pd-catalyzed
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