ASYMMETRIC CYCLOPROPANATION OF ALLYLIC ETHERS - CLEAVAGE AND REGENERATION OF THE CHIRAL AUXILIARY

被引：38

作者：

CHARETTE, AB

COTE, B

机构：

[1] Département de Chimie, Université de Montréal, Québec

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 04期

关键词：

D O I：

10.1021/jo00056a028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ring contraction reaction of 2-O-(trifluoromethyl)sulfonyl]oxy]-beta-D-glucopyranosides and their corresponding a-anomers is reported. The rearrangement was shown to occur under extremely mild basic conditions to allow isolation of acid-sensitive optically active substituted cyclopropylmethanols. The chiral auxiliary can be regenerated by converting the C-glucofuranoside, byproduct of the rearrangement, into tri-O-benzyl-D-glucal (two steps).

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页码：933 / 936

页数：4

相关论文

共 18 条

[1] A FACILE FORMATION OF 2,5-ANHYDRO SUGARS BY RING CONTRACTION IN METHYL HEXOPYRANOSIDE 2-TRIFLATES UNDER CONDITIONS OF NUCLEOPHILIC DISPLACEMENT [J].

BAER, HH ;

MATEO, FH ;

SIEMSEN, L .

CARBOHYDRATE RESEARCH, 1989, 187 (01) :67-92

[2] INVERSION OF CONFIGURATION IN 2,6-DIDEOXY SUGARS - TRIFLATE DISPLACEMENT BY BENZOATE AND NITRITE ANIONS [J].

BINKLEY, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3892-3896

[3] DESICCANT EFFICIENCY IN SOLVENT DRYING .3. DIPOLAR APROTIC-SOLVENTS [J].

BURFIELD, DR ;

SMITHERS, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) :3966-3968

[4] CARBOHYDRATES AS CHIRAL AUXILIARIES - ASYMMETRIC CYCLOPROPANATION REACTION OF ACYCLIC OLEFINS [J].

CHARETTE, AB ;

COTE, B ;

MARCOUX, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8166-8167

[5] CARBOHYDRATES AS CHIRAL AUXILIARIES - SYNTHESIS OF 2-HYDROXY-BETA-D-GLUCOPYRANOSIDES [J].

CHARETTE, AB ;

MARCOUX, JF ;

COTE, B .

TETRAHEDRON LETTERS, 1991, 32 (49) :7215-7218

[6] DIASTEREOSELECTIVE FREE-RADICAL REACTIONS .3. THE METHYL GLUCOPYRANOS-1-YL AND THE 1,2-O-ISOPROPYLIDENEGLUCOPYRANOS-1-YL RADICALS - CONFORMATIONAL EFFECTS ON DIASTEREOSELECTIVITY [J].

CRICH, D ;

LIM, LBL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09) :2209-2214

[7]

DESLONGCHAMPS P, 1983, STEREOELECTRONIC EFF, P183

[8] ENZYMATIC-HYDROLYSIS OF CYCLOPROPANES - TOTAL SYNTHESIS OF OPTICALLY PURE DICTYOPTERENE-A AND DICTYOPTERENE-C' [J].

GRANDJEAN, D ;

PALE, P ;

CHUCHE, J .

TETRAHEDRON, 1991, 47 (07) :1215-1230

[9]

Hanessian S, 1976, Adv Carbohydr Chem Biochem, V33, P111

[10] TOTAL SYNTHESIS AND STEREOCHEMICAL IDENTITY OF THE C18H32O5 DEGRADATION PRODUCT FROM BOROMYCIN [J].

HANESSIAN, S ;

TYLER, PC ;

DEMAILLY, G ;

CHAPLEUR, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6243-6246