A SHORT ROUTE TO A MOSHERS ACID PRECURSOR VIA CATALYTIC ASYMMETRIC DIHYDROXYLATION (AD)

被引：34

作者：

BENNANI, YL ^{[1
]}

VANHESSCHE, KPM ^{[1
]}

SHARPLESS, KB ^{[1
]}

机构：

[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 08期

关键词：

D O I：

10.1016/0957-4166(94)80116-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

alpha-Methoxy-alpha-(trifluoromethyl)phenyl acetic acid (MTPA) is a valuable derivatizing agent for enantiomeric excess determination of alcohols and amines. A short synthesis of a precursor to this compound, bared on the asymmetric dihydroxylation (AD) reaction is reported.

引用

收藏

页码：1473 / 1476

页数：4

相关论文

共 19 条

[1] SYNTHESES AND CRYSTAL-STRUCTURES OF THE CINCHONA ALKALOID DERIVATIVES USED AS LIGANDS IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].

AMBERG, W ;

BENNANI, YL ;

CHADHA, RK ;

CRISPINO, GA ;

DAVIS, WD ;

HARTUNG, J ;

JEONG, KS ;

OGINO, Y ;

SHIBATA, T ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) :844-849

[2] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[3] CHEMOENZYMATIC PREPARATION OF ATROLACTIC AND MOSHERS ACID USING ASPERGILLUS-ORYZAE PROTEASE [J].

FEICHTER, C ;

FABER, K ;

GRIENGL, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (03) :653-654

[4]

FRIED J, 1973, TETRAHEDRON LETT, V14, P3899

[5] MULTIPLE BONDS BETWEEN MAIN-GROUP ELEMENTS AND TRANSITION-METALS .107. CATALYTIC-OXIDATION OF PARTIALLY AND FULLY FLUORINATED OLEFINS WITH OSMIUM-TETROXIDE [J].

HERRMANN, WA ;

EDER, SJ ;

SCHERER, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (10) :1345-1347

[6]

HEYNS K, 1963, NEWER METHODS PREP, V2, P303

[7] A MODIFIED SYNTHESIS OF MOSHERS ACID AND ITS USE IN A SENSITIVE STEREOISOMER ANALYSIS OF AMINO-ACID DERIVATIVES [J].

HULL, WE ;

SEEHOLZER, K ;

BAUMEISTER, M ;

UGI, I .

TETRAHEDRON, 1986, 42 (02) :547-552

[8]

HUNDSCHEID FJA, 1987, TETRAHEDRON, V43, P5088

[9] TRIFLUOROISOPROPENYLZINC REAGENT AS A USEFUL ALPHA-(TRIFLUOROMETHYL)ETHENYL CARBANION SYNTHETIC EQUIVALENT - PREPARATION AND PALLADIUM-CATALYZED COUPLING WITH ARYL HALIDES [J].

JIANG, B ;

XU, YY .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26) :7336-7340

[10]

JIANG B, 1990, Patent No. 1061050