CATALYTIC ONE-POT OSMYLATION OF CYCLOHEXADIENES - STEREOCHEMICAL AND CONFORMATIONAL STUDIES OF THE RESULTING POLYOLS

被引：23

作者：

TSCHAMBER, T

BACKENSTRASS, F

FRITZ, H

STREITH, J

机构：

[1] Ecole Nationale Supérieure de Chimie, Université de Haute-Alsace, Mulhouse, F-68093, 3, rue Alfred Werner

[2] Physikalische Abteilung, Ciba, Geigy AG, Basel

来源：

HELVETICA CHIMICA ACTA | 1992年 / 75卷 / 04期

关键词：

D O I：

10.1002/hlca.19920750408

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H2O in the presence of the co-oxidant N-methylmorpholine N-oxide (NMO). The formation of polyols occurred stereospecifically with cyclohexadienes 3, 7, and 11 a, leading thereby to tetrols 5a, and 9a and to allo-inositol (14a), respectively. To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (neo), and 20a (chiro). High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.

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页码：1052 / 1060

页数：9

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