HOMOCHIRAL CYCLOADDUCTS DERIVED FROM SUGAR ALDOXIMES VIA NITRONE INTERMEDIATES

被引：14

作者：

FREDERICKSON, M

GRIGG, R

REDPATH, J

THORNTONPETT, M

机构：

[1] UNIV LEEDS,SCH CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND

[2] ORGANON RES LABS LTD,NEWHOUSE ML1 5SH,LANARK,SCOTLAND

来源：

TETRAHEDRON | 1994年 / 50卷 / 18期

关键词：

D O I：

10.1016/S0040-4020(01)80704-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tandem nitrone generation/cycloaddition reactions between simple sugar aldoximes and divinyl sulphone in refluxing toluene have been shown to occur regiospecifically and with high diastereoselectivity in the cycloaddition step to afford homochiral cycloadducts in good yield. The process is applicable to both furanose and pyranose aldoximes. Absolute stereochemistries of the products have been determined by NOE spectroscopy and X-ray crystallography.

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页码：5495 / 5502

页数：8

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