STEREOCONTROLLED 1,4-ASYMMETRIC REDUCTION OF CYCLIC HEMIKETALS - SYNTHESIS OF BOTH ANTI-1,4-DIOLS AND SYN-1,4-DIOLS, AND THEIR TRANSFORMATIONS INTO TRANS-2,5-DISUBSTITUTED TETRAHYDROFURANS AND CIS-2,5-DISUBSTITUTED TETRAHYDROFURANS

被引：4

作者：

CHIKASHITA, H

FUKUSHIMA, T

UEMURA, H

ITOH, K

机构：

来源：

CHEMISTRY LETTERS | 1992年 / 04期

关键词：

D O I：

10.1246/cl.1992.599

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reduction of dithioacetal-functionalized cyclic hemiketals with LiAlH4 in THF and NaBH4 in ethanol gave the corresponding anti- and syn-1,4-diols with excellent stereoselectivity, respectively. The anti- and syn-1,4-diols were easily transformed into trans- and cis-2,5-disubstituted tetrahydrofurans with complete stereospecificity by the one-step cyclodehydration with p-TsCl in pyridine, respectively.

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页码：599 / 602

页数：4

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