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KMID : 0366919940060010016
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Sungkyun Pharmceutical Journal
1994 Volume.6 No. 1 p.16 ~ p.20
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Study on the Isomerization of 2-Oxazolidone based on the Geometric Configuration
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Abstract
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The regioisomers of 2-oxazolidone ester 5 and 10 were prepared from cis-2-butene-1,4-diol as a starting material via epoxidation and cyclization. Isomerization of them by the intramolecular attack of the alkoxy moiety was investigated during the cleavage of ester moiety with sodium methoxide. Threo-oxazlidone ester 5 was converted to its corresponding alcohol 11 and then 11 was in situ isomerized to trans-oxazolidone alcohol 12 in 72% yield. Otherwise, erythro-oxazolidone ester 10 was converted to its corresponding alcohol 13 only without any isomerization.
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