Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates

被引：18

作者：

Beng, Timothy K. ^{[1
]}

Takeuchi, Hironori ^{[2
]}

Weber, Manuel ^{[3
]}

Sarpong, Richmond ^{[3
]}

机构：

[1] Susquehanna Univ, Dept Chem, Selinsgrove, PA 17870 USA

[2] Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan

[3] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 36期

基金：

美国国家卫生研究院;

关键词：

DIASTEREOSELECTIVE SYNTHESIS; CARBOLITHIATION; ALKYLATION; LITHIATION; DYNAMICS; DEPROTONATION; EQUIVALENTS; DERIVATIVES; CARBANIONS; REACTIVITY;

D O I：

10.1039/c5cc01307k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Substituted piperidines are emerging as important medicinally-active structural motifs. Here, we report highly stereoselective carbolithiation reactions of alpha-aryl piperidine enecarbamates that offer direct access to vicinally-substituted piperidine compounds. We have also demonstrated that the carbanion intermediates can be trapped with a carbon electrophile.

引用

页码：7653 / 7656

页数：4

共 45 条

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