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  • Title: Biomimetic Desymmetrization of a Carboxylic Acid.
    Author: Knowe MT, Danneman MW, Sun S, Pink M, Johnston JN.
    Journal: J Am Chem Soc; 2018 Feb 14; 140(6):1998-2001. PubMed ID: 29400455.
    Abstract:
    The enantioselective desymmetrization of carboxylic acids by chiral Brønsted base catalysis is reported, leading to bridged bicyclic lactones with up to 94% ee. Crystallographic analysis of a substrate-catalyst complex suggests an origin of stereocontrol, reminiscent of functional Brønsted bases in biological settings, and enabled reaction optimization. The products contain an all-carbon quaternary stereocenter and can be derivatized to functionalized cyclopentanes.
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