Improved preparation of alkyl 2-(3-indolyl)-3-nitroalkanoates under fully heterogeneous conditions:: stereoselective synthesis of alkyl (E)-2-(3-indolyl)-2-alkenoates

被引：26

作者：

Ballini, Roberto ^{[1
]}

Gabrielli, Serena ^{[1
]}

Palmieri, Alessandro ^{[1
]}

Petrini, Marino ^{[1
]}

机构：

[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy

来源：

TETRAHEDRON | 2008年 / 64卷 / 23期

关键词：

conjugate addition; heterogeneous catalysis; indoles; nitroaldol reaction; nitroalkenes;

D O I：

10.1016/j.tet.2008.04.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ethyl 3-nitro-2-alkenoates can be generated starting from nitroalkanes and ethyl 2-oxoacetate under heterogeneous conditions that minimize work-up procedures, avoid any purification step and direct manipulation of the nitroalkene system. Reaction of ethyl 3-nitro-2-alkenoates, formed in situ from their acetoxy precursors, with indoles in the presence of basic alumina affords ethyl 2-(3-indolyl)-3-nitro-alkanoates that are central intermediates for the preparation of tryptamines and carboline alkaloids. A base promoted elimination of nitrous acid from these nitroindolyl derivatives readily produces ethyl 2-(3-indolyl)-2-alkenoates with high E stereoselectivity. The latter compounds can be used as Michael acceptors in intra- and intermolecular reactions with nucleophilic reagents. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5435 / 5441

页数：7

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