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 in | Tetrahedron: asymmetry Vol. 15; no. 3; pp. 419 - 422 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
09.02.2004
Elsevier |
Subjects | |
Online Access | Get full text |
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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. |
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ISSN: | 0957-4166 1362-511X |
DOI: | 10.1016/j.tetasy.2003.12.022 |