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 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
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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| References | Parker, O’Fee (BIB9) 1983; 105 Williams, Abad Grillo, Comins (BIB7) 2002; 67 Agami, Couty (BIB6) 2002; 58 Jaouen, Jégou, Verières (BIB13) 1996 Jordá-Gregori, González-Rosende, Cava-Montesinos, Sepúlveda-Arques, Galeazzi, Orena, Jordá-Gregori, González-Rosende, Sepúlveda-Arques, Galeazzi, Orena (BIB3) 2000; 11 Walsh, Leslie, O’Shea, Botting, Chiba, Yanaqawa, Masubuchi, Kataoka, Kawaguchi, Ohtsuki, Hoshino, Enders, Haerting, Runsink, Guarnieri, Sendzik, Fröhlich, Hoppe, Gmeier, Kartner, Kamimura, Yoshihara, Marumo, Yamamoto, Nishiguchi, Kakehi, Kenzi (BIB1) 2002; 12 Sugimura, Miura, Yamada (BIB12) 1997; 8 Kemp, Bao, Pedersen (BIB10) 1996; 61 Foglia, Swern (BIB8) 1969; 34 Delle Monache, Misiti, Zappia, Avenoza, Cativiela, Fernádez-Recio, Peregrina, Guindon, Slassi, Rancourt, Bantle, Bencheqroun, Murtagh, Ghiro, Jung, Bongini, Cardillo, Orena, Porzi, Sandri, Kamiyana, Urano, Kobayashi, Ohno, Hirama, Iwashita, Yamakazi, Ito, Georges, Fraser-Reid, Kuivila (BIB4) 1999; 10 Garner, Park, Dondoni, Perrone, Delle Monache, Di Giovanni, Maggio, Misiti, Zappia, Meffre, Durand, Branquet, Le Goffic (BIB2) 1998; 24 Mc Killop, Taylor, Watson, Lewis, Moriwake, Hamano, Saito, Torii (BIB11) 1994 Paquette (BIB5) 1995; Vol. 7 Walsh, HA (WOS:000174145500024) 2002; 12 FOGLIA, TA (WOS:A1969D543600032) 1969; 34 KUIVILA HG (WOS:000188785400005.22) 1970 KAMIMURA, A (WOS:A1992JQ22700023) 1992; 57 GARNER P (WOS:000188785400005.10) 1998; 4 Sugimura, H (WOS:000071304500017) 1997; 8 PARKER, KA (WOS:A1983QB33800073) 1983; 105 Jorda-Gregori, JM (WOS:000080157500016) 1999; 10 Guarnieri, W (WOS:000075952000013) 1998 MORIWAKE, T (WOS:A1987K719500058) 1987 MEFFRE, P (WOS:A1994NW99900009) 1994; 24 GMEINER, P (WOS:A1995QD43300015) 1995 DELLEMONACHE, G (WOS:A1995RX37400022) 1995 Kemp, SJ (WOS:A1996VL34900064) 1996; 61 Jaouen, V (WOS:A1996WC21100028) 1996 Enders, D (WOS:000075809400008) 1998; 1998 Chiba, K (WOS:000073500000045) 1998; 160 Agami, C (WOS:000175065100001) 2002; 58 Jorda-Gregori, JM (WOS:000165324600015) 2000; 11 Williams, AL (WOS:000174489000037) 2002; 67 Dondoni, A (WOS:A1997XD51600009) 1997 HIRAMA, M (WOS:A1984TQ87200032) 1984; 25 BONGINI, A (WOS:A1987K646100014) 1987; 43 Avenoza, A (WOS:A1996UD02000023) 1996; 7 PAQUETTE LA (WOS:000188785400005.26) 1995 MCKILLOP, A (WOS:A1994MT14000006) 1994 KAMIYAMA, K (WOS:A1987H912900019) 1987; 28 Delle Monache, G (WOS:000082774100016) 1999; 10 GUINDON, Y (WOS:A1995QE61900002) 1995; 60 GEORGES, M (WOS:A1981MN69800019) 1981; 22 Moriwake (10.1016/j.tetasy.2003.12.022_BIB11_2) 1987 Kamimura (10.1016/j.tetasy.2003.12.022_BIB1_6) 1992; 57 Sugimura (10.1016/j.tetasy.2003.12.022_BIB12) 1997; 8 Kemp (10.1016/j.tetasy.2003.12.022_BIB10) 1996; 61 Jaouen (10.1016/j.tetasy.2003.12.022_BIB13) 1996 Enders (10.1016/j.tetasy.2003.12.022_BIB1_3) 1998; 9 Delle Monache (10.1016/j.tetasy.2003.12.022_BIB2_3) 1995 Meffre (10.1016/j.tetasy.2003.12.022_BIB2_4) 1994; 24 Williams (10.1016/j.tetasy.2003.12.022_BIB7) 2002; 67 Dondoni (10.1016/j.tetasy.2003.12.022_BIB2_2) 1997 Foglia (10.1016/j.tetasy.2003.12.022_BIB8) 1969; 34 Walsh (10.1016/j.tetasy.2003.12.022_BIB1_1) 2002; 12 Delle Monache (10.1016/j.tetasy.2003.12.022_BIB4_1) 1999; 10 Kamiyana (10.1016/j.tetasy.2003.12.022_BIB4_5) 1987; 28 Chiba (10.1016/j.tetasy.2003.12.022_BIB1_2) 1998; 160 Jordá-Gregori (10.1016/j.tetasy.2003.12.022_BIB3A) 2000; 11 Jordá-Gregori (10.1016/j.tetasy.2003.12.022_BIB3B) 1999; 10 Parker (10.1016/j.tetasy.2003.12.022_BIB9) 1983; 105 Mc Killop (10.1016/j.tetasy.2003.12.022_BIB11_1) 1994 Avenoza (10.1016/j.tetasy.2003.12.022_BIB4_2) 1996; 7 Paquette (10.1016/j.tetasy.2003.12.022_BIB5) 1995; Vol. 7 Guarnieri (10.1016/j.tetasy.2003.12.022_BIB1_4) 1998 Bongini (10.1016/j.tetasy.2003.12.022_BIB4_4) 1987; 43 Gmeier (10.1016/j.tetasy.2003.12.022_BIB1_5) 1995 Garner (10.1016/j.tetasy.2003.12.022_BIB2_1) 1998 Kuivila (10.1016/j.tetasy.2003.12.022_BIB4_8) 1970 Guindon (10.1016/j.tetasy.2003.12.022_BIB4_3) 1995; 60 Hirama (10.1016/j.tetasy.2003.12.022_BIB4_6) 1984; 25 Georges (10.1016/j.tetasy.2003.12.022_BIB4_7) 1981; 22 Agami (10.1016/j.tetasy.2003.12.022_BIB6) 2002; 58 |
| References_xml | – volume: 11 start-page: 3769 year: 2000 end-page: 3777 ident: BIB3 publication-title: Tetrahedron: Asymmetry contributor: fullname: Orena – volume: Vol. 7 year: 1995 ident: BIB5 publication-title: Encyclopedia of Reagents for Organic Synthesis contributor: fullname: Paquette – start-page: 31 year: 1994 end-page: 34 ident: BIB11 publication-title: Synthesis contributor: fullname: Torii – volume: 10 start-page: 2961 year: 1999 end-page: 2973 ident: BIB4 publication-title: Tetrahedron: Asymmetry contributor: fullname: Kuivila – volume: 34 start-page: 1680 year: 1969 end-page: 1684 ident: BIB8 publication-title: J. Org. Chem. contributor: fullname: Swern – volume: 61 start-page: 7162 year: 1996 end-page: 7167 ident: BIB10 publication-title: J. Org. Chem. contributor: fullname: Pedersen – start-page: 1218 year: 1996 end-page: 1220 ident: BIB13 publication-title: Synlett contributor: fullname: Verières – volume: 8 start-page: 4089 year: 1997 end-page: 4099 ident: BIB12 publication-title: Tetrahedron: Asymmetry contributor: fullname: Yamada – volume: 58 start-page: 2701 year: 2002 end-page: 2724 ident: BIB6 publication-title: Tetrahedron contributor: fullname: Couty – volume: 67 start-page: 1972 year: 2002 end-page: 1973 ident: BIB7 publication-title: J. Org. Chem. contributor: fullname: Comins – volume: 24 start-page: 300 year: 1998 end-page: 529 ident: BIB2 publication-title: Org. Synth. Coll. Vol. IX contributor: fullname: Le Goffic – volume: 12 start-page: 361 year: 2002 end-page: 363 ident: BIB1 publication-title: Bio. Med. Chem. Lett. contributor: fullname: Kenzi – volume: 105 start-page: 654 year: 1983 end-page: 655 ident: BIB9 publication-title: J. Am. Chem. Soc. contributor: fullname: O’Fee – volume: 8 start-page: 4089 year: 1997 ident: WOS:000071304500017 article-title: Enantiospecific and diastereoselective synthesis of syn-beta-amino-alpha-hydroxy acids publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Sugimura, H – volume: 10 start-page: 2961 year: 1999 ident: WOS:000082774100016 article-title: A stereocontrolled synthesis of (-)-detoxinine from L-ascorbic acid publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Delle Monache, G – start-page: 31 year: 1994 ident: WOS:A1994MT14000006 article-title: AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE GARNER ALDEHYDE AND ITS USE FOR THE SYNTHESIS OF N-PROTECTED 1-HALO-2-(R)-AMINO-3-BUTENES publication-title: SYNTHESIS-STUTTGART contributor: fullname: MCKILLOP, A – volume: 22 start-page: 4635 year: 1981 ident: WOS:A1981MN69800019 article-title: CIS - OXYAMINATION ROUTES TO AMINO-SUGARS - A SIMPLE SYNTHESIS OF HOLACOSAMINE publication-title: TETRAHEDRON LETTERS contributor: fullname: GEORGES, M – start-page: 1155 year: 1995 ident: WOS:A1995RX37400022 article-title: CONVENIENT PREPARATION OF O-BENZYL-N-CBZ-D-SERINOL, AN INTERMEDIATE IN BETA-HYDROXY-ALPHA-AMINO ACID SYNTHESIS publication-title: SYNTHESIS-STUTTGART contributor: fullname: DELLEMONACHE, G – volume: 105 start-page: 654 year: 1983 ident: WOS:A1983QB33800073 article-title: HALONIUM-INITIATED CYCLIZATIONS OF ALLYLIC URETHANES - STEREOSELECTIVITY AND REGIOSELECTIVITY IN FUNCTIONALIZING THE OLEFINIC BOND publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: PARKER, KA – volume: 12 start-page: 361 year: 2002 ident: WOS:000174145500024 article-title: 2-amino-4-[3 '-hydroxyphenyl]-4-hydroxybutanoic acid; A potent inhibitor of rat and recombinant human kynureninase publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS contributor: fullname: Walsh, HA – volume: 25 start-page: 4963 year: 1984 ident: WOS:A1984TQ87200032 article-title: CARBAMATE MEDIATED FUNCTIONALIZATION OF UNSATURATED ALCOHOLS .2. REGIO-SELECTIVE AND STEREO-SELECTIVE SYNTHESIS OF 1,3-SYN AND 1,2-ANTI AMINO ALCOHOL DERIVATIVES VIA IODOCARBAMATION publication-title: TETRAHEDRON LETTERS contributor: fullname: HIRAMA, M – volume: 28 start-page: 3123 year: 1987 ident: WOS:A1987H912900019 article-title: STEREOCONTROLLED SYNTHESIS OF 6-EPI-D-PURPUROSAMINE-B BY IODOCYCLOCARBAMATION OF A CHIRAL Z-OLEFIN DERIVED FROM L-ALANINE AND L-MALIC ACID publication-title: TETRAHEDRON LETTERS contributor: fullname: KAMIYAMA, K – volume: 34 start-page: 1680 year: 1969 ident: WOS:A1969D543600032 article-title: 2-OXAZOLIDONE FORMATION BY PYROLYSIS OF BETA-IODOCARBAMATES . A STEREOSELECTIVE REACTION publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: FOGLIA, TA – start-page: 527 year: 1997 ident: WOS:A1997XD51600009 article-title: Synthesis of N-(tert-butoxycarbonyl)-N,O-isopropylidene serinal from serine methyl ester by a reduction-oxidation sequence publication-title: SYNTHESIS-STUTTGART contributor: fullname: Dondoni, A – start-page: 499 year: 1970 ident: WOS:000188785400005.22 publication-title: SYNTHESIS-STUTTGART contributor: fullname: KUIVILA HG – volume: 61 start-page: 7162 year: 1996 ident: WOS:A1996VL34900064 article-title: Selective inversion of the proximal or distal hydroxyl groups in syn,syn-3-[N-(alkoxycarbonyl)amino] 1,2-diols via cyclic sulfates publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Kemp, SJ – volume: 43 start-page: 4377 year: 1987 ident: WOS:A1987K646100014 article-title: A NEW SYNTHESIS OF BOTH THE ENANTIOMERS OF 4-AMINO-3-HYDROXYBUTANOIC ACID (GABOB) AND MM2 CALCULATIONS FOR ROTAMERS OF THE INTERMEDIATE OXAZOLIDIN-2-ONES publication-title: TETRAHEDRON contributor: fullname: BONGINI, A – volume: 67 start-page: 1972 year: 2002 ident: WOS:000174489000037 article-title: A novel free-radical ring contraction of a cyclic carbamate publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0163290 contributor: fullname: Williams, AL – start-page: 83 year: 1995 ident: WOS:A1995QD43300015 article-title: 2-DIBENZYLAMINOBUTANE-1,4-DIOL - AN EFFECTIVE CHIRAL BUILDING-BLOCK FOR THE SYNTHESIS OF 1,2-AMINO ALCOHOLS publication-title: SYNTHESIS-STUTTGART contributor: fullname: GMEINER, P – volume: 10 start-page: 1135 year: 1999 ident: WOS:000080157500016 article-title: Highly regio- and stereoselective iodocyclization of chiral 3-alkoxycarbonyl-4-propenyl-2,2-dimethy-1,3-oxazolidines: a computational investigation publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Jorda-Gregori, JM – start-page: 1218 year: 1996 ident: WOS:A1996WC21100028 article-title: A novel approach to furanoid sugars via 1,4-iodocyclization of pyranoid D-galactal publication-title: SYNLETT contributor: fullname: Jaouen, V – volume: 24 start-page: 2147 year: 1994 ident: WOS:A1994NW99900009 article-title: A STRAIGHTFORWARD SYNTHESIS OF N-BOC-L-SERINAL AND N-BOC-L-THREONINAL ACETONIDES publication-title: SYNTHETIC COMMUNICATIONS contributor: fullname: MEFFRE, P – volume: 7 start-page: 721 year: 1996 ident: WOS:A1996UD02000023 article-title: Synthesis of a new enantiomerically pure constrained homoserine. publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Avenoza, A – start-page: 1274 year: 1998 ident: WOS:000075952000013 article-title: Regio- and stereoselective lithiation and C-substitution of (S)-2-(Dibenzylamino)-butane-1,4-diol via dicarbamates publication-title: SYNTHESIS-STUTTGART contributor: fullname: Guarnieri, W – start-page: 5017 year: 1995 ident: WOS:000188785400005.26 publication-title: ENCY REAGENTS ORGANI contributor: fullname: PAQUETTE LA – volume: 160 start-page: 5037 year: 1998 ident: WOS:000073500000045 article-title: FTY720, a novel immunosuppressant, induces sequestration of circulating mature lymphocytes by acceleration of lymphocyte homing in rats. I. FTY720 selectively decreases the number of circulating mature lymphocytes by acceleration of lymphocyte homing publication-title: JOURNAL OF IMMUNOLOGY contributor: fullname: Chiba, K – volume: 58 start-page: 2701 year: 2002 ident: WOS:000175065100001 article-title: The reactivity of the N-Boc protecting group: an underrated feature publication-title: TETRAHEDRON contributor: fullname: Agami, C – start-page: 2085 year: 1987 ident: WOS:A1987K719500058 article-title: A STRAIGHTFORWARD SYNTHESIS OF ALLYL AMINES FROM ALPHA-AMINO-ACIDS WITHOUT RACEMIZATION publication-title: CHEMISTRY LETTERS contributor: fullname: MORIWAKE, T – volume: 57 start-page: 5403 year: 1992 ident: WOS:A1992JQ22700023 article-title: LEWIS ACID PROMOTED STEREOSELECTIVE CARBON CARBON BOND FORMATION OF 3-FORMYL-DELTA-2-ISOXAZOLINES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: KAMIMURA, A – volume: 60 start-page: 288 year: 1995 ident: WOS:A1995QE61900002 article-title: ROLE OF SIGMA-DONATION IN THE STEREOCONTROL OF HYDROGEN-TRANSFER REACTIONS INVOLVING ACYCLIC RADICALS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: GUINDON, Y – volume: 1998 start-page: 1793 year: 1998 ident: WOS:000075809400008 article-title: Diastereo- and enantioselective synthesis of N-protected 2-amino 1,4-diols by an oxa Michael addition/1,3-dipolar cycloaddition protocol publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Enders, D – volume: 11 start-page: 3769 year: 2000 ident: WOS:000165324600015 article-title: 1,3-oxazin-2-ones vs tetrahydrofurans by iodocyclisation of 2-alkoxycarbonylamino-3-alken-1-ols publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Jorda-Gregori, JM – volume: 4 start-page: 300 year: 1998 ident: WOS:000188785400005.10 publication-title: ORG SYNTH COLL contributor: fullname: GARNER P – start-page: 1155 year: 1995 ident: 10.1016/j.tetasy.2003.12.022_BIB2_3 publication-title: Synthesis doi: 10.1055/s-1995-4069 contributor: fullname: Delle Monache – start-page: 527 year: 1997 ident: 10.1016/j.tetasy.2003.12.022_BIB2_2 publication-title: Synthesis doi: 10.1055/s-1997-1229 contributor: fullname: Dondoni – volume: 160 start-page: 5037 year: 1998 ident: 10.1016/j.tetasy.2003.12.022_BIB1_2 publication-title: J. Inmunol. contributor: fullname: Chiba – volume: 25 start-page: 4963 year: 1984 ident: 10.1016/j.tetasy.2003.12.022_BIB4_6 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)91270-5 contributor: fullname: Hirama – start-page: 2085 year: 1987 ident: 10.1016/j.tetasy.2003.12.022_BIB11_2 publication-title: Chem. Lett. doi: 10.1246/cl.1987.2085 contributor: fullname: Moriwake – volume: 58 start-page: 2701 year: 2002 ident: 10.1016/j.tetasy.2003.12.022_BIB6 publication-title: Tetrahedron doi: 10.1016/S0040-4020(02)00131-X contributor: fullname: Agami – volume: 8 start-page: 4089 year: 1997 ident: 10.1016/j.tetasy.2003.12.022_BIB12 publication-title: Tetrahedron: Asymmetry doi: 10.1016/S0957-4166(97)00595-8 contributor: fullname: Sugimura – volume: 7 start-page: 721 year: 1996 ident: 10.1016/j.tetasy.2003.12.022_BIB4_2 publication-title: Tetrahedron: Asymmetry doi: 10.1016/0957-4166(96)00067-5 contributor: fullname: Avenoza – volume: 34 start-page: 1680 year: 1969 ident: 10.1016/j.tetasy.2003.12.022_BIB8 publication-title: J. Org. Chem. doi: 10.1021/jo01258a032 contributor: fullname: Foglia – volume: 60 start-page: 288 year: 1995 ident: 10.1016/j.tetasy.2003.12.022_BIB4_3 publication-title: J. Org. Chem. doi: 10.1021/jo00107a002 contributor: fullname: Guindon – volume: 11 start-page: 3769 year: 2000 ident: 10.1016/j.tetasy.2003.12.022_BIB3A publication-title: Tetrahedron: Asymmetry doi: 10.1016/S0957-4166(00)00323-2 contributor: fullname: Jordá-Gregori – volume: 28 start-page: 3123 year: 1987 ident: 10.1016/j.tetasy.2003.12.022_BIB4_5 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)96301-9 contributor: fullname: Kamiyana – volume: 43 start-page: 4377 year: 1987 ident: 10.1016/j.tetasy.2003.12.022_BIB4_4 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)90313-8 contributor: fullname: Bongini – start-page: 499 year: 1970 ident: 10.1016/j.tetasy.2003.12.022_BIB4_8 publication-title: Synthesis doi: 10.1055/s-1970-21630 contributor: fullname: Kuivila – start-page: 83 year: 1995 ident: 10.1016/j.tetasy.2003.12.022_BIB1_5 publication-title: Synthesis doi: 10.1055/s-1995-3846 contributor: fullname: Gmeier – start-page: 1274 year: 1998 ident: 10.1016/j.tetasy.2003.12.022_BIB1_4 publication-title: Synthesis doi: 10.1055/s-1998-6099 contributor: fullname: Guarnieri – volume: 24 start-page: 2147 year: 1994 ident: 10.1016/j.tetasy.2003.12.022_BIB2_4 publication-title: Synth. Commun. doi: 10.1080/00397919408010228 contributor: fullname: Meffre – volume: 12 start-page: 361 year: 2002 ident: 10.1016/j.tetasy.2003.12.022_BIB1_1 publication-title: Bio. Med. Chem. Lett. doi: 10.1016/S0960-894X(01)00758-2 contributor: fullname: Walsh – volume: 57 start-page: 5403 year: 1992 ident: 10.1016/j.tetasy.2003.12.022_BIB1_6 publication-title: J. Org. Chem. doi: 10.1021/jo00046a023 contributor: fullname: Kamimura – volume: 10 start-page: 1135 year: 1999 ident: 10.1016/j.tetasy.2003.12.022_BIB3B publication-title: Tetrahedron: Asymmetry doi: 10.1016/S0957-4166(99)00084-1 contributor: fullname: Jordá-Gregori – volume: 61 start-page: 7162 year: 1996 ident: 10.1016/j.tetasy.2003.12.022_BIB10 publication-title: J. Org. Chem. doi: 10.1021/jo961060j contributor: fullname: Kemp – start-page: 31 year: 1994 ident: 10.1016/j.tetasy.2003.12.022_BIB11_1 publication-title: Synthesis doi: 10.1055/s-1994-25398 contributor: fullname: Mc Killop – volume: 22 start-page: 4635 year: 1981 ident: 10.1016/j.tetasy.2003.12.022_BIB4_7 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)83000-8 contributor: fullname: Georges – volume: Vol. 7 year: 1995 ident: 10.1016/j.tetasy.2003.12.022_BIB5 contributor: fullname: Paquette – volume: 105 start-page: 654 year: 1983 ident: 10.1016/j.tetasy.2003.12.022_BIB9 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00341a073 contributor: fullname: Parker – volume: 9 start-page: 1793 year: 1998 ident: 10.1016/j.tetasy.2003.12.022_BIB1_3 publication-title: Eur. J. Org. Chem. doi: 10.1002/(SICI)1099-0690(199809)1998:9<1793::AID-EJOC1793>3.0.CO;2-9 contributor: fullname: Enders – start-page: 1218 year: 1996 ident: 10.1016/j.tetasy.2003.12.022_BIB13 publication-title: Synlett doi: 10.1055/s-1996-5709 contributor: fullname: Jaouen – volume: 10 start-page: 2961 year: 1999 ident: 10.1016/j.tetasy.2003.12.022_BIB4_1 publication-title: Tetrahedron: Asymmetry doi: 10.1016/S0957-4166(99)00316-X contributor: fullname: Delle Monache – volume: 67 start-page: 1972 year: 2002 ident: 10.1016/j.tetasy.2003.12.022_BIB7 publication-title: J. Org. Chem. doi: 10.1021/jo0163290 contributor: fullname: Williams – start-page: 300 year: 1998 ident: 10.1016/j.tetasy.2003.12.022_BIB2_1 publication-title: Org. Synth. Coll. Vol. IX contributor: fullname: Garner |
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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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