Synthesis of tetrahydro-β-carbolines via isomerization of N-allyltryptamines: a metal-catalyzed variation on the Pictet-Spengler theme

被引：38

作者：

Ascic, Erhad ^{[1
]}

Hansen, Casper L. ^{[1
]}

Le Quement, Sebastian T. ^{[1
]}

Nielsen, Thomas E. ^{[1
]}

机构：

[1] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 27期

关键词：

RING-CLOSING METATHESIS; ACYLIMINIUM IONS; TANDEM CATALYSIS; ALKALOIDS; CHEMISTRY; SEQUENCE; BOND; STEREOSPECIFICITY; CONDENSATION; HETEROCYCLES;

D O I：

10.1039/c2cc17704h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient and broadly applicable alternative to the classical Pictet-Spengler synthesis of tetrahydro-beta-carbolines is presented. The method relies on metal-catalyzed isomerization of allylic amines to form reactive iminium intermediates which can be trapped by a tethered indole nucleophile.

引用

页码：3345 / 3347

页数：3

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