WITTIG-TYPE REACTIONS WITH PARTIALLY PROTECTED ALDOSES - SYNTHESIS OF ACYCLIC ALDOOCTENOATES AND OCTENONITRILES WITH E-STEREOCHEMISTRY

被引:8
作者
LIEVRE, C [1 ]
FRECHOU, C [1 ]
DEMAILLY, G [1 ]
机构
[1] FAC SCI AMIENS,CHIM ORGAN LAB,VALORISAT GLUCIDES GRP,F-80039 AMIENS,FRANCE
关键词
(CARBOMETHOXYMETHYL)TRIPHENYLPHOSPHONIUM YLIDE; PHOSPHONIUM SALT; METHYL BROMOACETATE; BROMOACETONITRILE; ALDOOCTENOATES; ALDOOCTENONITRILES;
D O I
10.1016/0040-4039(95)01305-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mono or di-protected aldoses react with methyl bromoacetate or bromoacetonitrile, in presence of tri-n-butylphosphine and zinc, to give stereoselectively with good yields the corresponding E unsaturated Wittig adducts.
引用
收藏
页码:6467 / 6470
页数:4
相关论文
共 18 条
[1]  
BANET AGM, 1986, J ORG CHEM, V51, P495
[2]  
BERHAN CH, 1983, ALDRICHIM ACTA, V16, P67
[3]   ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].
CHA, JK ;
CHRIST, WJ ;
KISHI, Y .
TETRAHEDRON, 1984, 40 (12) :2247-2255
[4]   STEREOCONTROLLED ROUTES TO FUNCTIONALIZED C-GLYCOPYRANOSIDES [J].
DAWE, RD ;
FRASERREID, B .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) :522-528
[5]   A NEW ROUTE TO C-GLYCOSYL COMPOUNDS - WITTIG-TYPE REACTION PROMOTED BY ZINC [J].
DHEILLY, L ;
FRECHOU, C ;
BEAUPERE, D ;
UZAN, R ;
DEMAILLY, G .
CARBOHYDRATE RESEARCH, 1992, 224 :301-306
[6]   SAMARIUM(II) IODIDE MEDIATED TRANSFORMATION OF CARBOHYDRATES TO CARBOCYCLES [J].
ENHOLM, EJ ;
TRIVELLAS, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6463-6465
[7]   STEREOSELECTIVE ROUTES TO SOME UNSATURATED ALPHA-C-GLYCOPYRANOSIDES AND BETA-C-GLYCOPYRANOSIDES [J].
FRASERREID, B ;
DAWE, RD ;
TULSHIAN, DB .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (13) :1746-1749
[8]   STEREOSELECTIVITY IN THE FORMATION OF UNSATURATED WITTIG PRODUCTS AND STEREOSPECIFICITY IN THEIR ELECTROPHILE INDUCED CYCLIZATION TO C-GLYCOSIDES [J].
HERRERA, FJL ;
GONZALEZ, MSP ;
SAMPEDRO, MN ;
ACIEGO, RMD .
TETRAHEDRON, 1989, 45 (01) :269-276
[9]   WITTIG REACTION OF UNPROTECTED D-ALDOPENTOSES WITH STABILIZED YLIDES - METAL-ION EFFECTS [J].
HORTON, D ;
KOH, D .
CARBOHYDRATE RESEARCH, 1993, 250 (02) :231-247
[10]   STEREOCONTROL IN DIELS-ALDER CYCLOADDITION TO UNSATURATED SUGARS - REACTIVITIES OF CIS-DIENOPHILES WITH CYCLOPENTADIENE [J].
HORTON, D ;
KOH, D ;
TAKAGI, Y .
CARBOHYDRATE RESEARCH, 1993, 250 (02) :261-274