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Pure Appl. Chem., 2012, Vol. 84, No. 8, pp. 1673-1684

Published online 2012-02-03

Accessing chemical diversity by stereoselective gold-catalyzed manipulation of allylic and propargylic alcohols

Gianpiero Cera, Michel Chiarucci and Marco Bandini*

Dipartimento di Chimica “G. Ciamician”, Alma Mater Studiorum, University of Bologna, Via Selmi 2, I‑40126 Bologna, Italy

Abstract: The combined use of asymmetric Au(I) catalysis with allylic as well as propargylic alcohols proved to be a competent synthetic tool, toward the realization of complex molecular organic architectures in a stereochemically defined manner. In particular, allylic alcohols have been utilized as alkylating agents in the synthesis of tetrahydrocarbazoles/carbolines and morpholines by means of new C–C and C–X bond-forming processes. Analogously, the direct activation of indole-propargylic alcohols with cationic Au complexes opened a direct access to tetracyclic fused indolines in a highly stereoselective manner.