Article ID Journal Published Year Pages File Type
1324893 Journal of Organometallic Chemistry 2011 10 Pages PDF
Abstract

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 CC (respect to allenes and alkynes) in taking part in nucleophilic additions assisted by π-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.

Graphical abstractThe efficient gold-catalyzed activation of allylic alcohols for the stereoselective alkylation of indoles is documented. Chiral MeOBIPHEP(AuX)2 complexes provided ready access to several classes of polycyclic indole compounds, i.e. tetrahydro-β-carbolines and tetrahydrocarbazoles, through intramolecular Friedel–Crafts-type allylic alkylation, in good yield and high enantiomeric excesses.Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights► Stereoselective hydroarylation of unactivated alkenes. ► Gold-catalyzed allylic alkylations of indoles with alcohols. ► Enantioselective synthesis of polycyclic indoles.

Related Topics
Physical Sciences and Engineering Chemistry Inorganic Chemistry
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