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2023•Chemical SynthesisRequires access

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

Jingcheng Guo, Ye Zhang, Xiaoxiang Zhang, Zhenqian Fu

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Abstract

The construction of d 3 -methylated all-carbon quaternary stereocenters has been successfully developed via carbene-catalyzed desymmetrization of prochiral d 3 -methylated oxindolyl 1,3-diketones. Three new stereogenic centers were efficiently constructed with satisfactory outcomes. Diverse spiro-polycyclic molecules with a d 3 -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.

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What this paper is about

The construction of d 3 -methylated all-carbon quaternary stereocenters has been successfully developed via carbene-catalyzed desymmetrization of prochiral d 3 -methylated oxindolyl 1,3-diketones. Three new stereogenic centers were efficiently constructed with satisfactory outcomes. Diverse spiro-polycyclic molecules with a d 3 -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.

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Available abstract

The construction of d 3 -methylated all-carbon quaternary stereocenters has been successfully developed via carbene-catalyzed desymmetrization of prochiral d 3 -methylated oxindolyl 1,3-diketones. Three new stereogenic centers were efficiently constructed with satisfactory outcomes. Diverse spiro-polycyclic molecules with a d 3 -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.

Key concepts: Stereocenter, Desymmetrization, Carbene, Catalysis, Chemistry, Carbon fibers, Stereochemistry, Combinatorial chemistry

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