PREPARATION AND REACTIONS OF ETHYL (R,R)-3-TRIFLUOROMETHYLOXIRANE-2-CARBOXYLATE AND (S,S)-3-TRIFLUOROMETHYLOXIRANE-2-CARBOXYLATE, A VERSATILE, EASILY ACCESSIBLE CF3-CONTAINING BUILDING BLOCK FOR SYNTHESIS

被引：10

作者：

BUSSCHEHUNNEFELD, CV ^{[1
]}

SEEBACH, D ^{[1
]}

机构：

[1] SWISS FED INST TECHNOL,ORGAN CHEM LAB,UNIV STR 16,CH-8092 ZURICH,SWITZERLAND

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 05期

关键词：

GLYCIDIC ESTERS; OXIRANECARBOXYLIC ESTERS; THREONINE; ALLO-THREONINE; EPOXY ALCOHOLS; FLUSTRATES; PAYNE REARRANGEMENT;

D O I：

10.1002/cber.19921250538

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile three-step route has been elaborated leading from 4,4,4-trifluoro-3-oxobutanoate to the trifluoro glycidic ester 1 mentioned in the title (0.1-mole scale). Reactions with azide (--> 4, 5) and with organometallic compounds such as cuprates (--> 3, 6), lithium (--> 7, 8), and magnesium derivatives (--> 9-11) furnish novel enantiomerically pure trifluoromethyl-substituted carboxylic esters, ketones, diols, and epoxy alcohols. The latter ones undergo selective isomerizations by Payne rearrangement (11 --> 12) in aqueous NaOH/acetone or tert-butyl alcohol.

引用

页码：1273 / 1281

页数：9

共 42 条

[1]

ACS M, 1990, CHIMIA, V44, P90

[2]

AEBI JD, 1984, LIEBIGS ANN CHEM, P407

[3]

AEBI JD, 1983, LIEBIGS ANN CHEM, P2114

[4]

BECK AK, 1990, CHIMIA, V44, P291

[5]

Behrens C. H., 1983, ALDRICHIM ACTA, V16, P67

[6] PREPARATION AND PROPERTIES OF CHIRAL FLUOROORGANIC COMPOUNDS [J].

BRAVO, P ;

RESNATI, G .

TETRAHEDRON-ASYMMETRY, 1990, 1 (10) :661-692

[7]

BUSSCHEHUNNEFEL.CV, 1992, THESIS ETH ZURICH

[8] ABOUT THE STEREOSPECIFIC ALPHA-ALKYLATION OF BETA-HYDROXYESTERS [J].

FRATER, G .

HELVETICA CHIMICA ACTA, 1979, 62 (08) :2825-2828

[9] STEREOSPECIFIC SYNTHESIS OF (+)-(3R,4R)-4-METHYL-3-HEPTANOL - ENANTIOMER OF A PHEROMONE OF THE SMALLER EUROPEAN ELM BARK BEETLE (SCOLYTUS-MULTISTRIATUS) [J].

FRATER, G .

HELVETICA CHIMICA ACTA, 1979, 62 (08) :2829-2832

[10] REGIO-SPECIFIC AND STEREO-SPECIFIC SYNTHESIS OF THREO-3-AMINO-2-HYDROXY-ACIDS, NOVEL AMINO-ACIDS CONTAINED IN AMINOPEPTIDASE INHIBITORS OF MICROBIAL ORIGIN [J].

KATO, K ;

SAINO, T ;

NISHIZAWA, R ;

TAKITA, T ;

UMEZAWA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (07) :1618-1621

← 1 2 3 4 5 →