Allylic alcohols: Valuable synthetic equivalents of non-activated alkenes in gold-catalyzed enantioselective alkylation of indoles

被引：53

作者：

Bandini, Marco ^{[1
]}

Gualandi, Andrea ^{[1
]}

Monari, Magda ^{[1
]}

Romaniello, Alessandro ^{[1
]}

Savoia, Diego ^{[1
]}

Tragni, Michele ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2011年 / 696卷 / 01期

关键词：

Allylic alcohols; Friedel-Crafts reaction; Gold-catalysis; Indole; Stereoselection; FRIEDEL-CRAFTS ALKYLATION; C-H BONDS; ORGANIC-REACTIONS; HYDROARYLATION; ALKALOIDS; PLATINUM; ALLENES; HETEROCYCLES; METATHESIS; ALLYLATION;

D O I：

10.1016/j.jorganchem.2010.09.065

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The recent booming of gold catalysis has demonstrated that unprecedented transformations can be realized in a highly selective manner. Moreover, due to the growing availability of chiral organic ligands, gold-catalysis can be considered as one of most dynamic hot spots in asymmetric synthesis. However, in this context, the use of non-activated olefinic C-C double bonds is still largely unexplored due to the intrinsic inertness of C=C (respect to allenes and alkynes) in taking part in nucleophilic additions assisted by pi-electrophilic activations. Allylic alcohols have been demonstrated to be feasible "surrogates" of non-activated alkenes for the enantioselective allylic alkylation of indoles catalyzed by chiral gold(I) complexes. In this investigation, a full account addressing efficiency and substrate scope of such a process is presented. (C) 2010 Elsevier B.V. All rights reserved.

引用

页码：338 / 347

页数：10

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