INDIUM-MEDIATED ALLYLATION OF ALDEHYDES - A CONVENIENT ROUTE TO 2-DEOXY AND 2,6-DIDEOXY CARBOHYDRATES

被引：55

作者：

BINDER, WH ^{[1
]}

PRENNER, RH ^{[1
]}

SCHMID, W ^{[1
]}

机构：

[1] UNIV WIEN,INST ORGAN CHEM,A-1090 VIENNA,AUSTRIA

来源：

TETRAHEDRON | 1994年 / 50卷 / 03期

关键词：

D O I：

10.1016/S0040-4020(01)80790-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity. Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated. The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.

引用

页码：749 / 758

页数：10

共 26 条

[1] CYCLOPROPANATION OF ELECTRON-DEFICIENT ALKENES AND WIDEQVIST-TYPE SYNTHESIS OF CYCLOPROPANES MEDIATED BY INDIUM METAL
ARAKI, S
BUTSUGAN, Y
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (17) : 1286 - 1287
[2] ALLYLATION OF CARBONYL-COMPOUNDS WITH CATALYTIC AMOUNT OF INDIUM
ARAKI, S
JIN, SJ
IDOU, Y
BUTSUGAN, Y
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (06) : 1736 - 1738
[3] SYNTHESIS OF BETA-HYDROXYESTERS BY REFORMATSKY REACTION USING INDIUM METAL
ARAKI, S
ITO, H
BUTSUGAN, Y
[J]. SYNTHETIC COMMUNICATIONS, 1988, 18 (04) : 453 - 458
[4] PREPARATION AND SOME REACTIONS OF ALLYLIC INDIUM REAGENTS
ARAKI, S
SHIMIZU, T
JOHAR, PS
JIN, SJ
BUTSUGAN, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) : 2538 - 2542
[5] INDIUM-MEDIATED ALLYLATION OF ALDIMINES
BEUCHET, P
LEMARREC, N
MOSSET, P
[J]. TETRAHEDRON LETTERS, 1992, 33 (40) : 5959 - 5960
[6] A CONCISE CHEMICAL SYNTHESIS OF (+)-3-DEOXY-D-GLYCERO-D-GALACTO-NONULOSONIC ACID (KDN)
CHAN, TH
LI, CJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (10) : 747 - 748
[7] ACYLKETENE [4+2] CYCLOADDITIONS - DIVERGENT DENOVO SYNTHESIS OF 2,6-DIDEOXY SUGARS
COLEMAN, RS
FRASER, JR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) : 385 - 392
[8] STUDIES IN STEREOCHEMISTRY .10. THE RULE OF STERIC CONTROL OF ASYMMETRIC INDUCTION IN THE SYNTHESES OF ACYCLIC SYSTEMS
CRAM, DJ
ELHAFEZ, FAA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (23) : 5828 - 5835
[9] ULTRASOUND IN ORGANIC-SYNTHESIS .13. SOME FUNDAMENTAL-ASPECTS OF THE SONOCHEMICAL BARBIER REACTION
DESOUZABARBOZA, JC
PETRIER, C
LUCHE, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) : 1212 - 1218
[10] STEREOCHEMISTRY AND SYNTHETIC APPLICATIONS OF THE PRODUCTS OF YEAST REDUCTION OF 3-HYDROXY-3-METHYL-5-PHENYLPENT-4-EN-2-ONE
FRONZA, G
FUGANTI, C
PEDROCCHIFANTONI, G
SERVI, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) : 1141 - 1144

← 1 2 3 →