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Updated: May 27, 2025
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Catalytic Enantioconvergent Alkylation Reactions That Construct Chiral Quaternary Carbon Centers and Tune
Muhammad Sohail1, Keisuke Kobayashi2, Hiroshi Tomoda2
1Chemistry and Chemical Bioengineering Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna, Okinawa, 904-0495, Japan.
Abstract:
In molecules with central chiral centers functionalized with aryl groups, the rotation of the single bond between the aryl group and the central chiral center may be hindered. Enantioconvergent alkylation reactions of racemic diastereomers to construct all-carbon quaternary stereocenters resulting in easing of the rotation around the axes are described. We demonstrated that the rotation of the bond between a central chiral carbon center and a dihydrobenzofuranone can be tuned by selection of either a tertiary carbon bearing a hydrogen or a quaternary carbon at the central chiral center. The products have the benefits of a central chiral center and a flexibly rotatable bond, which can facilitate interactions with other molecules.
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