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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

Pemberton, Nils (author)
Umeå universitet,Kemiska institutionen
Emtenäs, Hans (author)
Umeå universitet,Kemiska institutionen
Boström, Dan (author)
Umeå universitet,Kemiska institutionen
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Domaille, Peter J (author)
Greenberg, William A (author)
Levin, Michael D (author)
Zhu, Zuolin (author)
Almqvist, Fredrik (author)
Umeå universitet,Kemiska institutionen
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 (creator_code:org_t)
2005-02-17
2005
English.
In: Organic Letters. - Washington, D.C. : American Chemical Society. - 1523-7060 .- 1523-7052. ; 7:6, s. 1019-1021
  • Journal article (peer-reviewed)
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  • 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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