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Synthesis 2017; 49(21): 4738-4744
DOI: 10.1055/s-0036-1588802
DOI: 10.1055/s-0036-1588802
special topic
Copper(I)-Catalyzed Boryl Substitution of Allyl Aminals: Selective Synthesis of Linear γ-Aminoallylboronates
This study was financially supported by the MEXT (Japan) program (Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions) of Hokkaido University, as well asFurther Information
Publication History
Received: 08 February 2017
Accepted after revision: 30 March 2017
Publication Date:
15 May 2017 (online)
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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588802.
- Supporting Information
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