6533b85dfe1ef96bd12bf1ad

RESEARCH PRODUCT

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

José Sepúlveda-arquesM. Eugenia González-rosendeMario OrenaJ. Miquel Jorda-gregori

subject

Inorganic Chemistrychemistry.chemical_compoundHydrolysisEthanolchemistryBicyclic moleculeOrganic ChemistryOrganic chemistryHydroxymethylTributyltin hydridePhysical and Theoretical ChemistryTolueneCatalysis

description

Abstract 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.

yearjournalcountryeditionlanguage
2004-02-01Tetrahedron: Asymmetry
https://doi.org/10.1016/j.tetasy.2003.12.022