Copper(I)-Catalyzed Boryl Substitution of Allyl Aminals: Selective Synthesis of Linear γ-AminoallylboronatesThis study was financially supported by the MEXT (Japan) program (Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions) of Hokkaido University, as well as
Received: 08 February 2017
Accepted after revision: 30 March 2017
15 May 2017 (eFirst)
Published as part of the Special Topic Modern Strategies for Borylation in Synthesis
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).