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

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