THE ABSOLUTE-CONFIGURATION OF 6,8-DIOXABICYCLO[3.2.1]OCTANE AND SEVERAL METHYL-SUBSTITUTED DERIVATIVES

被引：35

作者：

IBRAHIM, N ^{[1
]}

EGGIMANN, T ^{[1
]}

DIXON, EA ^{[1
]}

WIESER, H ^{[1
]}

机构：

[1] UNIV CALGARY, DEPT CHEM, CALGARY T2N 1N4, ALBERTA, CANADA

来源：

TETRAHEDRON | 1990年 / 46卷 / 05期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4020(01)81959-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiomers of 6,8-dioxabicyclo[3.2.1]octane and the alkyl substituted derivatives, exo- and endo-7-methyl, exo- and endo-5,7-dimethyl, 7,7-dimethyl, and exo- and endo-7-ethyl-5-methyl (exo- and endo-brevicomin), were synthesized stereoselectively with known configuration by standard synthetic methods, or with baker's yeast, or both. The correlation between the absolute configuration of the bicyclic rings and the optical rotation was established by means of chiral complexation gas chromatography for two molecules for which this correlation was not known previously. In all cases, the (1R) enantiomer exhibits positive rotation. The absolute configurations were established for the yeast products which were always produced in high optical purity. © 1990.

引用

页码：1503 / 1514

页数：12

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