Construction of Enantioenriched 4,5,6,7‐Tetrahydrofuropyridines through a Multicatalytic Sequence Merging Gold and Amine Catalysis

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...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-10, Vol.363 (19), p.4516-4520
Main Authors: Genet, Manon, Takfaoui, Abdelilah, Marrot, Jérôme, Greck, Christine, Moreau, Xavier
Format: Article
Language:English
Subjects:
Aldehydes
Catalysis
Cycloaddition
Gold
Isomerization
Pyridines
Stereoselectivity
Substrates
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100756