RADICAL CYCLIZATION OF ALLYL PROPARGYL ETHERS AND ACETALS - APPLICATION TO THE STEREOCONTROLLED ACYLATION OF CARBOHYDRATES

被引：26

作者：

MOUFID, N ^{[1
]}

CHAPLEUR, Y ^{[1
]}

机构：

[1] UNIV NANCY 1,CNRS,CHIM ORGAN LAB,BP239,F-54506 VANDOEUVRE NANCY,FRANCE

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(00)74333-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Stannylvinyl radicals are stereospecifically cyclised onto olefinic carbohydrates to give vinylstannanes, which are further elaborated to ketones. This sequence allows the stereospecific acylation of unsaturated carbohydrates at C-2 or C-3 in good yields under mild conditions.

引用

页码：1799 / 1802

页数：4

共 46 条

[11] STEREOSELECTIVE C-C BOND FORMATION IN CARBOHYDRATES BY RADICAL CYCLIZATION REACTIONS .4. APPLICATION FOR THE SYNTHESIS OF ALPHA-C(1)-GLUCOSIDES
DEMESMAEKER, A
HOFFMANN, P
ERNST, B
HUG, P
WINKLER, T
[J]. TETRAHEDRON LETTERS, 1989, 30 (46) : 6311 - 6314
[12] DEMESMAEKER A, 1990, SYNLETT, P201
[13] STEREOSELECTIVE C-C BOND FORMATION IN CARBOHYDRATES BY RADICAL CYCLIZATION REACTIONS .2.
DEMESMAEKER, A
HOFFMANN, P
ERNST, B
[J]. TETRAHEDRON LETTERS, 1989, 30 (01) : 57 - 60
[14] STEREOSELECTIVE C-C BOND FORMATION IN CARBOHYDRATES BY RADICAL CYCLIZATION REACTIONS .3. STRATEGY FOR THE PREPARATION OF C(1)-GLYCOSIDES
DEMESMAEKER, A
HOFFMANN, P
ERNST, B
HUG, P
WINKLER, T
[J]. TETRAHEDRON LETTERS, 1989, 30 (46) : 6307 - 6310
[15] STEREOSELECTIVE C-C BOND FORMATION IN CARBOHYDRATES BY RADICAL CYCLIZATION REACTIONS-I
DEMESMAEKER, A
HOFFMANN, P
ERNST, B
[J]. TETRAHEDRON LETTERS, 1988, 29 (50) : 6585 - 6588
[16] RADICAL ANOMERIC CHEMISTRY
DESCOTES, G
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (01) : 1 - 20
[17] FORMATION OF C-GLYCOSIDES BY A PALLADIUM-CATALYZED COUPLING REACTION OF TRIBUTYLSTANNYL GLYCALS WITH ORGANIC HALIDES
DUBOIS, E
BEAU, JM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (17) : 1191 - 1192
[18] RADICAL CYCLIZATION REACTIONS LEADING TO DOUBLY BRANCHED CARBOHYDRATES AND 6-OXYGENATED AND 8-OXYGENATED 2,9-DIOXABICYCLO[4.3.0]NONANE DERIVATIVES
FERRIER, RJ
PETERSEN, PM
TAYLOR, MA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (17) : 1247 - 1248
[19] THE PREPARATION OF C-ARYLGLYCALS - THE PALLADIUM-CATALYZED COUPLING OF 3,4,6-TRI-O-(TERT-BUTYLDIMETHYLSILYL)-1-(TRIBUTYLSTANNYL)-D-GLUCAL AND ARYL BROMIDES
FRIESEN, RW
STURINO, CF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) : 2572 - 2574
[20] BIOMIMETIC CHAIN ELONGATION OF CARBOHYDRATES VIA RADICAL CARBON-CARBON BOND FORMATION
GIESE, B
LINKER, T
MUHN, R
[J]. TETRAHEDRON, 1989, 45 (04) : 935 - 940

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