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- Pemberton, Nils, et al.
(författare)
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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
- 2005
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Ingår i: Organic Letters. - Washington, D.C. : American Chemical Society. - 1523-7060 .- 1523-7052. ; 7:6, s. 1019-1021
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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- Åberg, Veronica, et al.
(författare)
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Synthesis and absolute configuration of methyl (-)-(3R)-8-(4-bromophenyl)-7-(naphthalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylate
- 2002
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Ingår i: Acta Crystallographica Section E. - 1600-5368. ; 58:8, s. 812-814
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Tidskriftsartikel (refereegranskat)abstract
- The title molecule, C26H20BrNO3S, contains a ring-fused 2-pyridinone framework substituted with a 4-bromo-phenyl-, a naphthalen-1-ylmethyl and a methoxycarbonyl substituent. The main goal of this work was to confirm the stereochemistry for the methoxycarbonyl substituent, which proved to be 3R. Moreover, the 4-bromophenyl substituent was shown to be rotated out of the plane of the 2-pyridinone ring, with a torsion angle of 61.2 (5)°. To allow the best packing arrangement, the naphthalen-1-ylmethyl substituent is positioned to mediate an intermolecular - interaction.
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