Catalytic Enantioselective Desymmetrization of Cyclobutane-1,3-diones by Carbonyl-Amine Condensation
Kai‐Ge Wen, Chao Liu, Donghui Wei, Yanfei Niu, Yiyuan Peng, Xing‐Ping Zeng
Abstract
A chiral phosphoric acid-catalyzed enantioselective condensation of 2,2-disubstituted cyclobutane-1,3-diones with a primary amine is described. This reaction offered a mild and efficient protocol for constructing quaternary carbon-containing cyclobutanes in good to high yields and enantioselectivities. This reaction is the first catalytic desymmetrizing carbonyl-amine condensation reaction and also represents the first catalytic desymmetrizing reaction of prochiral cyclobutane-1,3-dione.
Topics & Concepts
CyclobutaneChemistryDesymmetrizationEnantioselective synthesisCyclobutanesCatalysisAmine gas treatingOrganic chemistryMedicinal chemistryRing (chemistry)Asymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods