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Enantioselective Copper-Catalyzed Methylboration of Alkenes

Posted on 2018-02-20 - 20:16
An enantioselective Cu-catalyzed borylative cross-coupling reaction of alkenes, bis­(pinacolato)­diboron (B2(pin)2), and methyl iodide is reported. Alkenes including styrenes, β-substituted styrenes, and challenging aliphatic olefins were smoothly transferred to the desired methylboration products with excellent diastereoselectivities (dr up to >99:1) and enantioselectivities (er up to 99:1). The utility of this process was demonstrated by the synthesis of naproxen and formal synthesis of two natural products.

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