Direct construction of d₃-methylated all-carbon quaternary stereocenters through carbene-catalyzed desymmetrization

Abstract

The construction of d₃-methylated all-carbon quaternary stereocenters has been successfully developed via carbene-catalyzed desymmetrization of prochiral d₃-methylated oxindolyl 1,3-diketones. Three new stereogenic centers were efficiently constructed with satisfactory outcomes. Diverse spiro-polycyclic molecules with a d₃-methylated all-carbon quaternary stereocenter were generated in good to excellent yields with good to excellent diastereoselectivities and excellent enantioselectivities. This reaction features a broad substrate scope, good functional-group tolerance, and easy scale-up.

Keywords

d₃-Methylated / all-carbon quaternary stereocenters / N-Heterocyclic carbene / organocatalysis / desymmetrization

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