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

作者：Bandini Marco^*; Gualandi Andrea; Monari Magda; Romaniello Alessandro; Savoia Diego; Tragni Michele

来源：Journal of Organometallic Chemistry, 2011, 696(1): 338-347.

DOI：10.1016/j.jorganchem.2010.09.065

• Allylic alcohols
• Friedel-Crafts reaction
• Gold-catalysis
• Indole
• Stereoselection

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.

• 出版日期2011-1-1