Wittig-type reaction on unprotected aldoses -: Synthesis of α,β-unsaturated esters

被引:13
作者
Le Mignot, V [1 ]
Lièvre, C [1 ]
Fréchou, C [1 ]
Demailly, G [1 ]
机构
[1] Univ Picardie, Fac Sci, Chim Organ Lab, F-80039 Amiens, France
关键词
D O I
10.1016/S0040-4039(97)10721-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unprotected aldoses react with methylbromoacetate in presence of n-tributylphosphine and zinc to give stereoselectively with good yields the corresponding E unsaturated Wittig adducts. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:983 / 984
页数:2
相关论文
共 13 条
[1]  
BERHAN CH, 1983, ALDRICHIM ACTA, V16, P67
[2]   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
[3]   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
[4]  
DMITRIEV BA, 1967, ZH OBSHCH KHIM, V8, P2483
[5]   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
[6]   WITTIG REACTION OF UNPROTECTED D-ALDOPENTOSES WITH STABILIZED YLIDES - METAL-ION EFFECTS [J].
HORTON, D ;
KOH, D .
CARBOHYDRATE RESEARCH, 1993, 250 (02) :231-247
[7]   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
[8]   STEREOCONTROL IN DIELS-ALDER CYCLOADDITION TO UNSATURATED SUGARS - REACTIVITIES OF ACYCLIC 7-CARBON TRANS DIENOPHILES DERIVED FROM ALDOPENTOSES [J].
HORTON, D ;
KOH, D .
CARBOHYDRATE RESEARCH, 1993, 250 (02) :249-260
[9]   NEW ROUTE TO HIGHER SUGARS [J].
KOCHETKOV, NK ;
DMITRIEV, BA .
TETRAHEDRON, 1965, 21 (04) :803-+
[10]   Synthesis of 1,2-cis-C-glycofuranosides derived from non-protected aldoses [J].
Lievre, C ;
Humez, S ;
Frechou, C ;
Demailly, G .
TETRAHEDRON LETTERS, 1997, 38 (34) :6003-6006