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

Published as part of the Special Topic Modern Strategies for Borylation in Synthesis

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).

Key words

allylboronates - copper - catalysis - 1,2-amino alcohols - allylboration

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