ZINC-COPPER COUPLE PROMOTED C-BRANCHING IN THE CARBOHYDRATE SERIES

被引:12
作者
BLANCHARD, P
DASILVA, AD
FOURREY, JL
MACHADO, AS
ROBERTGERO, M
机构
[1] CNRS,INST CHIM SUBSTANCES NAT,F-91198 GIF SUR YVETTE,FRANCE
[2] UNIV FED MINAS GERAIS,DEPT QUIM,BR-31270 BELO HORIZON,MG,BRAZIL
关键词
ALKYL IODIDE; CARBOHYDRATE; ZINC-COPPER COUPLE; RADICAL;
D O I
10.1016/S0040-4039(00)74719-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient C-branching at 3-position of di-O-isopropylidene glucose was readily accomplished by the zinc/copper couple induced conjugate addition of its 3-iodo derivative to various activated olefins at room temperature in a protic solvent mixture.
引用
收藏
页码:8069 / 8072
页数:4
相关论文
共 16 条
[1]   NITROGEN TRANSFER TO CARBON RADICALS [J].
BARTON, DHR ;
JASZBERENYI, JC ;
THEODORAKIS, EA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5904-5905
[2]   SYNTHESIS OF DEOXYHALOGENO SUGARS - DISPLACEMENT OF THE (TRIFLUOROMETHANESULFONYL)OXY (TRIFLYL) GROUP BY HALIDE ION [J].
BINKLEY, RW ;
AMBROSE, MG ;
HEHEMANN, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (22) :4387-4391
[3]   A CONJUGATE ADDITION OF PRIMARY ALKYL IODIDE DERIVED SPECIES TO ELECTRON DEFICIENT OLEFINS [J].
BLANCHARD, P ;
ELKORTBI, MS ;
FOURREY, JL ;
ROBERTGERO, M .
TETRAHEDRON LETTERS, 1992, 33 (23) :3319-3322
[4]   SOME C-C BOND CONSTRUCTIONS ON MONOSACCHARIDES USING COBALOXIME-MEDIATED RADICAL ALKYL-NITROALKYLANION CROSS COUPLING REACTIONS [J].
BRANCHAUD, BP ;
YU, GX .
TETRAHEDRON LETTERS, 1991, 32 (30) :3639-3642
[5]   ULTRASOUND IN ORGANIC SYNTHESES .19. FURTHER-STUDIES ON THE CONJUGATE ADDITIONS TO ELECTRON DEFICIENT OLEFINS IN AQUEOUS-MEDIA [J].
DUPUY, C ;
PETRIER, C ;
SARANDESES, LA ;
LUCHE, JL .
SYNTHETIC COMMUNICATIONS, 1991, 21 (05) :643-651
[6]   1,2-STEREOINDUCTION IN RADICALS AND ANIONS - A COMPARISON BETWEEN HYDROGEN ABSTRACTION AND PROTONATION [J].
ERDMANN, P ;
SCHAFER, J ;
SPRINGER, R ;
ZEITZ, HG ;
GIESE, B .
HELVETICA CHIMICA ACTA, 1992, 75 (02) :638-644
[7]  
GARREGG PJ, 1980, J CHEM SOC P1, P2866
[8]   THE SCOPE OF RADICAL CC-COUPLING BY THE TIN METHOD [J].
GIESE, B ;
GONZALEZGOMEZ, JA ;
WITZEL, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (01) :69-70
[9]   FREE RADICAL-INDUCED C-ALLYLATION OF ALPHA-BROMOLACTONES - SYNTHESIS OF 2-C-ALLYL-2-DEOXY-D-ARABINONO-1,4-LACTONE AND 2-C-ALLYL-2-DEOXY-D-RIBONO-1,4-LACTONE [J].
HANESSIAN, S ;
LEGER, R ;
ALPEGIANI, M .
CARBOHYDRATE RESEARCH, 1992, 228 (01) :145-155
[10]   SYNTHESIS OF SOME 17-SUBSTITUTED 3,10-ETHANO-5ALPHA-ESTRANES [J].
HAUSER, FM ;
PHILIP, A ;
CARROLL, FI .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (21) :3696-3700