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

• Published in: Tetrahedron: 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
• Language: English
• 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

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...