A chiral Lewis base catalyzed enantioselective -allylic alkylation of 2-hydroxypyridines and MBH carbonates is documented, affording a convenient access to -alkylated 2-pyridones with up to 99% ee and 99% yield. Experimental and computational studies have revealed that the strong hydrogen bond interaction between the chiral Lewis base catalyst and 2-hydroxypyridines plays a crucial role in this reaction for the reactivity, chemoselectivity, and enantioselectivity.
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