Cycloaddition of delta2-thiazolines and acyl ketenes under acidic conditions results in bicyclic 1,3-oxazinones and not 6-acylpenams as earlier reported |
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Authors: | Pemberton Nils Emtenäs Hans Boström Dan Domaille Peter J Greenberg William A Levin Michael D Zhu Zuolin Almqvist Fredrik |
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Affiliation: | Organic Chemistry and Inorganic Chemistry, Ume? University, S-901 87 Ume?, Sweden. |
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Abstract: | [reaction: see text] Optically active Delta(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 beta-lactams, the optically active isomers 3R,9R-1,3-oxazinones 3a-g are obtained stereoselectively in 38-93% yields. |
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