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Potassium 2‐oxo‐3‐enoates as Effective and Versatile Surrogates for α, β‐Unsaturated Aldehydes in NHC‐Catalyzed Asymmetric Reactions
Author(s) -
Gao Yaru,
Ma Yafei,
Xu Chen,
Li Lin,
Yang Tianjian,
Sima Guoqing,
Fu Zhenqian,
Huang Wei
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701413
Subject(s) - chemistry , catalysis , substrate (aquarium) , potassium , combinatorial chemistry , organic chemistry , geology , oceanography
Potassium 2‐oxo‐3‐enoates, which are readily prepared at scale and easily stored, have been found to be effective and versatile surrogates for α,β‐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 CO 2 and then undergo asymmetric reactions via homoenolate and α, β‐unsaturated acyl azolium intermediate. The reactions have broad substrate scopes with high enantioselectivities.