Stereoselective piperidine synthesis through oxidative carbon-hydrogen bond functionalizations of enamides

被引：52

作者：

Brizgys, Gediminas J. ^{[1
]}

Jung, Hyung Hoon ^{[1
]}

Floreancig, Paul E. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

CHEMICAL SCIENCE | 2012年 / 3卷 / 02期

关键词：

N-ACYLIMINIUM IONS; AZA-PRINS-CYCLIZATION; ACTIVATION; DECARBOXYLATION; NEOPELTOLIDE; GENERATION; AZACYCLES; CHEMISTRY; ALDEHYDES; PEPTIDES;

D O I：

10.1039/c1sc00670c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Vinyl amides, carbamates, and sulfonamides that contain pendent p-nucleophiles react with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form piperidine structures with good to excellent levels of efficiency and stereocontrol. Reactions proceed nearly instantaneously at room temperature. Transition state models show the preferred configuration around the intermediate acyliminium ion and the orientation of the nucleophile.

引用

页码：438 / 442

页数：5

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