A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel-Crafts reactions

被引：30

作者：

Angeli, Marco ^{[1
]}

Bandini, Marco ^{[1
]}

Garelli, Andrea ^{[1
]}

Piccinelli, Fabio ^{[1
]}

Tommasi, Simona ^{[1
]}

Umani-Ronchi, Achille ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 17期

关键词：

D O I：

10.1039/b607864h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical catalytic approach to the synthesis of 4-substituted 1,2,3,4-tetrahydro-beta-carbolines (THBCs, 1) and 1,2,3,9-tetrahydropyrano[3,4-b] indoles ( 2) via InBr3-catalyzed intramolecular Friedel - Crafts ( F - C) cyclization is described. The use of cross-metathesis reaction represents a direct route to the cyclization precursors and the use of InBr3 ( 5 mol%) allowed polycyclic indole compounds to be isolated in high yields under mild reaction conditions (rt, DCM, minutes). Finally, efforts toward the development of a stereocontrolled version of the present cyclization are presented, highlighting [salenAlCl] and bimetallic [(salenAlCl)(2) - InBr3] system as promising chiral Lewis acids (ee up to 60%).

引用

页码：3291 / 3296

页数：6

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