Asymmetric Synthesis of β-Aminoboronates via Copper-Catalyzed Reductive Coupling of Vinyl Boronates with Imines.
Jing HeCham Bi SeoWan Seok YoonJaesook YunPublished in: Organic letters (2023)
We report a copper-catalyzed asymmetric reductive coupling of vinyl boronates with imines, which directly access enantiomerically enriched β-aminoalkylboronates. Stereoselective addition of the in situ generated chiral α-borylalkyl copper to N -phosphinoyl imines provided target products in good yields with high diastereo- and enantioselectivity. Vinyl boronate with methylated acenaphthoquinone as a boron ligand was essential to efficiently spawn asymmetric products, and organic transformations of the boron moiety, along with the easily removable N -protecting group, proved their synthetic utility.
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