Potassium 2-oxo-3-enoates as Effective and Versatile Surrogates for [alpha], [beta]-Unsaturated Aldehydes in NHC-Catalyzed Asymmetric Reactions

Potassium 2-oxo-3-enoates, which are readily prepared at scale and easily stored, have been found to be effective and versatile surrogates for [alpha],[beta]-unsaturated aldehydes in NHC-catalyzed asymmetric reactions. Promoted by chiral N-heterocyclic carbenes combined with LiCl, these easy-to-hand...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-02, Vol.360 (3), p.479
Main Authors: Gao, Yaru, Ma, Yafei, Xu, Chen, Li, Lin, Yang, Tianjian, Sima, Guoqing, Fu, Zhenqian, Huang, Wei
Format: Article
Language:English
Subjects:
Aldehydes
Asymmetry
Carbenes
Carbon dioxide
Chemical reactions
Lithium chloride
Potassium
Substrates
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Summary:Potassium 2-oxo-3-enoates, which are readily prepared at scale and easily stored, have been found to be effective and versatile surrogates for [alpha],[beta]-unsaturated aldehydes in NHC-catalyzed asymmetric reactions. Promoted by chiral N-heterocyclic carbenes combined with LiCl, these easy-to-handle solid salts could release of CO2 and then undergo asymmetric reactions via homoenolate and [alpha], [beta]-unsaturated acyl azolium intermediate. The reactions have broad substrate scopes with high enantioselectivities.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701413