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 CeC 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 p-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.

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

BANDINI, MARCO;GUALANDI, ANDREA;MONARI, MAGDA;SAVOIA, DIEGO;TRAGNI, MICHELE
2011

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 CeC 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 p-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.
M. Bandini; A. Gualandi; M. Monari; A. Romaniello; D. Savoia; M. Tragni
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/93568
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