An Enantioselective Ketene-Imine Cycloaddition Method for Synthesis of Substituted Ring-Fused 2-Pyridinones
2001 (English)In: The Journal of Organic Chemistry, Vol. 66, no 20, 6756-61 p.Article in journal (Refereed) Published
Previously, a method for the stereoselective synthesis of -lactams, starting from 2H-2-thiazolines and Meldrum's acid derivatives, has been reported from our laboratory. We now report a new method for the synthesis of optically active, highly substituted ring-fused 2-pyridinones. This was discovered when 2-alkyl-2-thiazolines and Meldrum's acid derivatives were treated with HCl(g) in benzene at 5 78 C. Further refinement of the synthetic protocol revealed that use of 1,2-dichloroethane as solvent at 0 64 C led to the desired 2-pyridinones in good yields and with excellent enantioselectivity. Use of these conditions allowed preparation of 2-pyridinones from several different 2-thiazolines and Meldrum's acid derivatives and may be a general route to 2-pyridinones.
Place, publisher, year, edition, pages
2001. Vol. 66, no 20, 6756-61 p.
IdentifiersURN: urn:nbn:se:umu:diva-9584DOI: doi:10.1021/jo015794uOAI: oai:DiVA.org:umu-9584DiVA: diva2:149255