Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 26, Issue 5, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202201318
Keywords
acyliminium ion; diastereoselectivity; enamide; nitrogen heterocycles; synthetic methods
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This article describes a stereoselective synthesis of isoindolo[2,1-a]quinolin-11(5H)-ones that contain three contiguous stereogenic centers. The desired fused heterocyclic isoindolinones are obtained in high yields and diastereoselectivities through a Lewis-acid mediated reaction of enamides with N-aryl-acylimines. The scope and limitations of this method are discussed. The stereochemical outcome of this transformation indicates a stepwise reaction pathway.
A stereoselective synthesis of isoindolo[2,1-a]quinolin-11(5H)-ones containing three contiguous stereogenic centers is described. This Lewis-acid mediated reaction of enamides with N-aryl-acylimines affords the desired fused heterocyclic isoindolinones in high yields and diastereoselectivities. Scope and limitations of this method are discussed. The stereochemical outcome of this transformation indicates a stepwise reaction pathway.
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