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 |
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Elsevier Ltd
09.02.2004
Elsevier |
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Abstract | 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. |
---|---|
AbstractList | 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. Reduction of (4S,5S,6S)-4-hydroxymethyl-5-iodo-6-methyl-1,3-oxazin-2-one 2a and (4S,5S,6R)-4-hydroxyrncthyl-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[3a,d]-1,3-oxazolidin-2-one 5 as the sole product. (C) 2003 Elsevier Ltd. All rights reserved. |
Author | Sepúlveda-Arques, José González-Rosende, M.Eugenia Jordá-Gregori, J.Miquel Orena, Mario |
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CitedBy_id | crossref_primary_10_1021_ja407027e crossref_primary_10_1039_D4RA03467H crossref_primary_10_1016_j_tet_2010_03_113 crossref_primary_10_1021_ol2001057 |
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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... Reduction of (4S,5S,6S)-4-hydroxymethyl-5-iodo-6-methyl-1,3-oxazin-2-one 2a and (4S,5S,6R)-4-hydroxyrncthyl-5-iodo-6-phenyl-1,3-oxazin-2-one 2b with... |
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SubjectTerms | Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Chemistry, Physical Physical Sciences Science & Technology |
Title | Novel enantiomerically pure 2-amino-1,4-diols from chiral 4-hydroxymethyl-5-iodo-1,3-oxazin-2-ones |
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