Stereoselective synthesis of allylic sulfones via the oxonia-Cope rearrangement of homoallylic alcohols containing a homoallylic sulfone moiety

被引：8

作者：

Jung, Se-Young ^{[1
]}

Min, Jae-Hong ^{[1
]}

Oh, Jung Taek ^{[1
]}

Koo, Sangho ^{[1
]}

机构：

[1] Myong Ji Univ, Dept Nano Sci & Engn, Dept Chem, Kyunggido 449728, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 13期

关键词：

D O I：

10.1021/jo060517e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The homoallylic alcohols 3 that can be prepared by the indium-mediated addition of haloallylic sulfones 1 to aldehydes 2 undergo the oxonia-Cope rearrangement with aldehydes 2 to give rise to the allylic sulfones 4 containing a conjugated diene moiety in a highly stereoselective manner. Electron-rich aldehydes preferentially participate in this oxonia-Cope rearrangement with the homoallylic alcohols 3. Excellent correlations of the stereochemistry ( anti-3 to trans-allylic sulfone 4 and syn-3 to cis-allylic sulfone 4) have been observed in the oxonia-Cope rearrangement.

引用

页码：4823 / 4828

页数：6

共 26 条

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