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Cycloaddition of 2-thiazolines and acyl ketenes under acidic conditions results in bicyclic 1,3-oxazinones and not 6-acylpenams as earlier reported
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
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2005 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 7, no 6, 1019-1021 p.Article in journal (Refereed) Published
Abstract [en]

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.
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URN: urn:nbn:se:umu:diva-14752DOI: 10.1021/ol047528jOAI: oai:DiVA.org:umu-14752DiVA: diva2:154424
Available from: 2008-03-27 Created: 2008-03-27 Last updated: 2017-12-14Bibliographically approved

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Pemberton, NilsEmtenäs, HansBoström, DanAlmqvist, Fredrik
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