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  • Title: Guanidine-Copper Complex Catalyzed Allylic Borylation for the Enantioconvergent Synthesis of Tertiary Cyclic Allylboronates.
    Author: Ge Y, Cui XY, Tan SM, Jiang H, Ren J, Lee N, Lee R, Tan CH.
    Journal: Angew Chem Int Ed Engl; 2019 Feb 18; 58(8):2382-2386. PubMed ID: 30615241.
    Abstract:
    An enantioconvergent synthesis of chiral cyclic allylboronates from racemic allylic bromides was achieved by using a guanidine-copper catalyst. The allylboronates were obtained with high γ/α regioselectivities (up to 99:1) and enantioselectivities (up to 99 % ee), and could be further transformed into diverse functionalized allylic compounds without erosion of optical purity. Experimental and DFT mechanistic studies support an SN 2' borylation process catalyzed by a monodentate guanidine-copper(I) complex that proceeds through a special direct enantioconvergent transformation mechanism.
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