PREPARATION OF OXAZOLIDIN-2-ONES BY OXIDATION OF OXAZOLIDINE-2-THIONES - A PROTON MAGNETIC-RESONANCE STRUCTURAL STUDY

被引：27

作者：

MORENOMANAS, M

PADROS, I

机构：

[1] Department of Chemistry, Universital Autònoma de Barcelona, Barcelona, 08193, Bellaterra

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1993年 / 30卷 / 05期

关键词：

D O I：

10.1002/jhet.5570300511

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of a series of oxazolidine-2-thiones, both homochiral and racemic, as well as their oxidation to oxazolidin-2-ones is reported. X-Ray and pmr studies have showed that the stereochemical integrity of the starting aminoalcohol is maintained.

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页码：1235 / 1239

页数：5

相关论文

共 26 条

[11] DIASTEREOSELECTIVE ALDOL REACTIONS USING BETA-KETO IMIDE DERIVED ENOLATES - A VERSATILE APPROACH TO THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS [J].

EVANS, DA ;

CLARK, JS ;

METTERNICH, R ;

NOVACK, VJ ;

SHEPPARD, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :866-868

[12] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[13] SYNTHESIS OF THE CYCLIC HEXAPEPTIDE ECHINOCANDIN-D - NEW APPROACHES TO THE ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY ALPHA-AMINO-ACIDS [J].

EVANS, DA ;

WEBER, AE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7151-7157

[14] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].

EVANS, DA ;

ENNIS, MD ;

MATHRE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739

[15] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030

[16]

Fujita E., 1989, ADV HETEROCYCL CHEM, V45, P1

[17]

Gage J. R., 1989, ORG SYNTH, V68, P77

[18] METALATED NITROGEN DERIVATIVES OF CARBONIC-ACID IN ORGANIC-SYNTHESIS .8. 2-THIOXO-OXAZOLIDINES BY CYCLOADDITION OF ALPHA-METALATED ALKYL ISOTHIOCYANATES TO CARBONYL-COMPOUNDS [J].

HOPPE, D ;

FOLLMANN, R .

CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (09) :3047-3061

[19] THE USE OF CYSTEINE-DERIVED AND SERINE-DERIVED THIAZOLIDINETHIONES AND OXAZOLIDINETHIONES AS EFFICIENT CHIRAL AUXILIARIES IN ALDOL CONDENSATIONS [J].

HSIAO, CN ;

LIU, L ;

MILLER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) :2201-2206

[20] AMINO ALCOHOL AND AMINO SUGAR SYNTHESIS BY BENZOYLCARBAMATE CYCLIZATION [J].

KNAPP, S ;

KUKKOLA, PJ ;

SHARMA, S ;

DHAR, TGM ;

NAUGHTON, ABJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5700-5710