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Construction of Enantioenriched 4,5,6,7‐Tetrahydrofuro[2,3‐ b ]pyridines through a Multicatalytic Sequence Merging Gold and Amine Catalysis

Authors :
Abdelilah Takfaoui
Manon Genet
Christine Greck
Jérôme Marrot
Xavier Moreau
Institut Lavoisier de Versailles (ILV)
Université de Versailles Saint-Quentin-en-Yvelines (UVSQ)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Source :
Advanced Synthesis and Catalysis, Advanced Synthesis and Catalysis, Wiley-VCH Verlag, In press, ⟨10.1002/adsc.202100756⟩
Publication Year :
2021
Publisher :
Wiley, 2021.

Abstract

International audience; A series of enantioenriched 4,5,6,7-tetrahydrofuro[2,3-b]pyridines were accessed by a cycloisomerization/cycloaddition strategy. Starting from ynamide derivatives and aldehydes, yields ranging from 27 to 90% and high levels of stereoselectivity (de>95%, 93–99% ee) were obtained through sequential relay catalysis. The concurrent use of a gold complex with a diphenylprolinol silyl ether was applied to a combination of diversely functionalized substrates.

Details

ISSN :
16154169 and 16154150
Volume :
363
Database :
OpenAIRE
Journal :
Advanced Synthesis & Catalysis
Accession number :
edsair.doi.dedup.....6334a4de422e0bb574e8f3d99f1b79fe
Full Text :
https://doi.org/10.1002/adsc.202100756