Synthesis 2017; 49(21): 4738-4744
DOI: 10.1055/s-0036-1588802
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Yuta Takenouchi, Hajime Ito*
  • Division of Applied Chemistry and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido, 060-8628, Japan   Email: hajito@eng.hokudai.ac.jp
This study was financially supported by the MEXT (Japan) program (Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions) of Hokkaido University, as well as
Further Information

Publication History

Received: 08 February 2017

Accepted after revision: 30 March 2017

Publication Date:
15 May 2017 (eFirst)

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).

Supporting Information

 
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