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Chemo-Selective Cross Reaction of Two Enals via Carbene-Catalyzed Dual Activations

Abstract

A dual catalytic chemo-selective cross-coupling reaction of two enals is developed. One enal (without α-substitution) is activated by an NHC catalyst to form an acylazolium enolate intermediate that undergoes Michael-type addition to another enal molecule bearing an alkynyl substituent. Mechanistic studies indicate that non-covalent interactions between the alkynyl enal and an NHC•HX catalyst play important roles in substrate activation and enantioselectivity control. Multiple of the possible side reactions are not observed. Our reaction provides highly chemo- and diastereo-selective access to chiral lactones containing functionalizable 1,3-enyn units with excellent enantioselectivities (95 to > 99% ee).

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Article information


Submitted
13 Jun 2020
Accepted
17 Sep 2020
First published
18 Sep 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Accepted Manuscript
Article type
Edge Article

Chemo-Selective Cross Reaction of Two Enals via Carbene-Catalyzed Dual Activations

X. Peng, J. Xu, T. Li, Y. R. Chi and Z. JIN, Chem. Sci., 2020, Accepted Manuscript , DOI: 10.1039/D0SC03297B

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