Nucleophilic substitution reactions of sulfur-substituted cyclohexanone acetals: An analysis of the factors controlling stereoselectivity

被引：29

作者：

Billings, Susan B. ^{[1
]}

Woerpel, K. A. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92696 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 14期

关键词：

D O I：

10.1021/jo060077r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The reactions of cyclohexanone acetals substituted with thiophenyl groups ( and other heteroatoms) at C-2 demonstrate the powerful influence that these substituents have on the stereoselectivity of nucleophilic substitution reactions. The trans selectivities of these reactions correlate with the behavior of the corresponding ketones. These experiments lend support to the possibility that the reactions of the acetals, which proceed via oxocarbenium ions, are operating under Felkin-Anh control.

引用

页码：5171 / 5178

页数：8

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