SUGARS AS CHIRAL AUXILIARIES FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE COMPOUNDS

被引:24
作者
REISSIG, HU
机构
[1] Institut Für Organische Chemie, Technischen Hochschule Darmstadt, D-W-6100
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1992年 / 31卷 / 03期
关键词
D O I
10.1002/anie.199202881
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The large number of functional groups and stereogenic centers was the main reason why sugar and sugar derivatives were hardly ever employed as chiral auxiliaries in asymmetric syntheses. Recent publications on highly enantioselective reactions performed with sugar auxiliaries (alkylations, aldol additions, amino acid syntheses, cyclopropanations, and Diels-Alder reactions) show that this reticence was unjustified. What is more, these compounds are, as a rule, easily accessible and inexpensive. They are thus predestined for a much wider use in asymmetric synthesis.
引用
收藏
页码:288 / 290
页数:3
相关论文
共 29 条
[1]  
ARNOLD T, UNPUB
[2]  
ARNOLD T, UNPUB ANGEW CHEM
[3]   ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL ALKOXYCYCLOHEXADIENES [J].
BIRD, CW ;
LEWIS, A .
TETRAHEDRON LETTERS, 1989, 30 (45) :6227-6228
[4]  
BRAUN H, 1991, TETRAHEDRON, V47, P3312
[5]   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
[6]   CYCLO-ADDITION OF ISOQUINOLINIUM SALTS - HOMOCHIRAL TETRALINS VIA DIENOPHILES BEARING CHIRAL AUXILIARIES [J].
CHOUDHURY, A ;
FRANCK, RW ;
GUPTA, RB .
TETRAHEDRON LETTERS, 1989, 30 (37) :4921-4924
[7]   SYNTHESIS OF OLIGOSACCHARIDES BY CYCLOADDITIONS .4. STEREOCHEMISTRY OF CYCLOADDITION OF CHIRAL ALCOHOLS TO BUTADIENYL ETHERS - 4 AND 6 DERIVATIVES OF PERBENZYL GLUCOSIDES [J].
DAVID, S ;
LUBINEAU, A ;
THIEFFRY, A .
TETRAHEDRON, 1978, 34 (03) :299-304
[8]  
DOTZ KH, 1990, NACHR CHEM TECH LAB, V38, P1244
[9]  
DUHAMEL L, 1991, SYNLETT, P807
[10]   ASYMMETRIC C-C-BOND FORMATION WITH TITANIUM CARBOHYDRATE COMPLEXES [J].
DUTHALER, RO ;
HAFNER, A ;
RIEDIKER, M .
PURE AND APPLIED CHEMISTRY, 1990, 62 (04) :631-642