A new method for the determination of the absolute stereochemistry of aromatic and heteroaromatic alkanols using Mosher's esters

被引：55

作者：

Kelly, DR ^{[1
]}

机构：

[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(99)00295-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A list of the H-1 NMR chemical shifts of the methoxy group of alpha-methoxy-alpha-(trifluoromethyl)phenylacetic acid (Mosher's) esters of alpha- and beta-(hetero)aromatic secondary alkanols has been compiled. Methoxy groups which are orientated syn to the (hetero)aromatic group in Mosher's conformational model have lower chemical shift values than those in the anti-orientation. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2927 / 2934

页数：8

共 39 条

[1]

AKITA H, 1984, CHEM PHARM BULL, V32, P1333

[2] Convenient asymmetric syntheses of anti-beta-amino alcohols [J].

Barrett, AGM ;

Seefeld, MA ;

White, AJP ;

Williams, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2677-2685

[3] ENZYMATIC RESOLUTION OF TRANS-2-ARYLCYCLOHEXAN-1-OLS USING CRUDE CHICKEN LIVER ESTERASE (CCLE) AS BIOCATALYST [J].

BASAVAIAH, D ;

RAO, PD .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :223-234

[4] A PSEUDOMONAS SP ALCOHOL-DEHYDROGENASE WITH BROAD SUBSTRATE-SPECIFICITY AND UNUSUAL STEREOSPECIFICITY FOR ORGANIC-SYNTHESIS [J].

BRADSHAW, CW ;

FU, H ;

SHEN, GJ ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1526-1532

[5] ADDITIONS OF CHIRAL ALLYLTITANOCENES TO ALDEHYDES - DIASTEREOSELECTIVE SYNTHESIS OF HOMOALLYLIC ALCOHOLS WITH A RECYCLABLE CHIRAL TRANSITION-METAL REAGENT [J].

COLLINS, S ;

KUNTZ, BA ;

HONG, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4154-4158

[6] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[7] A NEW ASYMMETRIC-SYNTHESIS OF CYANOHYDRINS AND OXYGEN-FUNCTIONALIZED DERIVATIVES - STEREOSELECTIVE ADDITION OF CYANIDE TO CHIRAL RHENIUM ALDEHYDE AND KETONE COMPLEXES OF THE FORMULA [(ETA-5-C5H5)RE(NO)(PPH3)(O=CRR')]+BF4- [J].

DALTON, DM ;

GARNER, CM ;

FERNANDEZ, JM ;

GLADYSZ, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6823-6829

[8] ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED BENZYL ALCOHOLS VIA THE STEREOSELECTIVE ADDITION OF NUCLEOPHILES TO HOMOCHIRAL TRICARBONYL(ETA-6-O-TRIALKYLSILYLBENZALDEHYDE)CHROMIUM(O) COMPLEXES [J].

DAVIES, SG ;

GOODFELLOW, CL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02) :393-407

[9]

Eidenhammer G, 1996, SYNTHESIS-STUTTGART, P748

[10] STEREOSELECTIVE ADDITION OF CYANIDE ION TO CHIRAL RHENIUM PI-ALDEHYDE COMPLEXES OF THE FORMULAS [(ETA-5-C5H5)RE(NO)(PPH3)(ETA-2-O=CHR)]+BF4- - A NEW SYNTHESIS OF OPTICALLY-ACTIVE CYANOHYDRIN DERIVATIVES [J].

GARNER, CM ;

FERNANDEZ, JM ;

GLADYSZ, JA .

TETRAHEDRON LETTERS, 1989, 30 (30) :3931-3934

← 1 2 3 4 →