Cycloaddition of 2-thiazolines and acyl ketenes under acidic conditions results in bicyclic 1,3-oxazinones and not 6-acylpenams as earlier reported
2005 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 7, no 6, 1019-1021 p.Article in journal (Refereed) Published
Optically active 2-thiazolines 4 were previously reported to react with acyl Meldrum's acid derivatives 5 under acidic conditions (HCl (g) in benzene) to stereoselectively give 6-acylpenams 1. Recently we have discovered that the structure elucidation of these compounds was incorrect. Thus, we report new data showing that instead of acyl -lactams, the optically active isomers 3R,9R-1,3-oxazinones 3a-g are obtained stereoselectively in 38-93% yields.
Place, publisher, year, edition, pages
Washington, D.C.: American Chemical Society , 2005. Vol. 7, no 6, 1019-1021 p.
IdentifiersURN: urn:nbn:se:umu:diva-14752DOI: 10.1021/ol047528jOAI: oai:DiVA.org:umu-14752DiVA: diva2:154424