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  • Title: Catalytic Regio- and Enantioselective Remote Hydrocarboxylation of Unactivated Alkenes with CO2.
    Author: Zhou L, Li L, Zhang S, Kuang XK, Zhou YY, Tang Y.
    Journal: J Am Chem Soc; 2024 Jul 17; 146(28):18823-18830. PubMed ID: 38950377.
    Abstract:
    The catalytic regio- and enantioselective hydrocarboxylation of alkenes with carbon dioxide is a straightforward strategy to construct enantioenriched α-chiral carboxylic acids but remains a big challenge. Herein we report the first example of catalytic highly enantio- and site-selective remote hydrocarboxylation of a wide range of readily available unactivated alkenes with abundant and renewable CO2 under mild conditions enabled by the SaBOX/Ni catalyst. The key to this success is utilizing the chiral SaBOX ligand, which combines with nickel to simultaneously control both chain-walking and the enantioselectivity of carboxylation. This process directly furnishes a range of different alkyl-chain-substituted or benzo-fused α-chiral carboxylic acids bearing various functional groups in high yields and regio- and enantioselectivities. Furthermore, the synthetic utility of this methodology was demonstrated by the concise synthesis of the antiplatelet aggregation drug (R)-indobufen from commercial starting materials.
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