Copper(I)-Catalyzed Boryl Substitution of Allyl Aminals: Selective Synthesis of Linear γ-Aminoallylboronates

Abstract A novel approach for the selective synthesis of α-substituted γ-aminoallylboronates through a copper(I)-catalyzed γ-boryl-substitution of allyl aminals is developed. The reaction proceeds with high yield (up to 88%) and good E / Z selectivity (up to >95:5). Subsequent aldehyde allylation using allylboronates affords ( Z )- anti -1,2-amino alcohol derivatives with high stereoselectivity (up to 91% yield, and up to 17:83 E / Z ).