Novel enantiomerically pure 2-amino-1,4-diols from chiral 4-hydroxymethyl-5-iodo-1,3-oxazin-2-ones

Graphic Reduction of (4 S,5 S,6 S)-4-hydroxymethyl-5-iodo-6-methyl-1,3-oxazin-2-one 2a and (4 S,5 S,6 R)-4-hydroxymethyl-5-iodo-6-phenyl-1,3-oxazin-2-one 2b with tributyltin hydride in ethanol afforded 1,3-oxazin-2-one 3a and 1,3-oxazolidin-2-one 4b , respectively. Hydrolysis of 3a and 4b under basi...

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Published inTetrahedron: asymmetry Vol. 15; no. 3; pp. 419 - 422
Main Authors González-Rosende, M.Eugenia, Jordá-Gregori, J.Miquel, Sepúlveda-Arques, José, Orena, Mario
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.02.2004
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
INTERMEDIATE
ACID
SUGARS
STEREOCONTROLLED SYNTHESIS
STRAIGHTFORWARD SYNTHESIS
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Summary:Graphic Reduction of (4 S,5 S,6 S)-4-hydroxymethyl-5-iodo-6-methyl-1,3-oxazin-2-one 2a and (4 S,5 S,6 R)-4-hydroxymethyl-5-iodo-6-phenyl-1,3-oxazin-2-one 2b with tributyltin hydride in ethanol afforded 1,3-oxazin-2-one 3a and 1,3-oxazolidin-2-one 4b , respectively. Hydrolysis of 3a and 4b under basic conditions led to enantiomerically pure aminodiols 1a and 1b . Reduction of 2b in refluxing toluene led to the unexpected bicyclic tetrahydrofuro[3 a, d]-1,3-oxazolidin-2-one 5 as the sole product.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2003.12.022