Au(Ⅰ)-Catalyzed Annulation of Enantioenriched Allenes in the Enantioselective Total Synthesis of (-)-Rhazinilam

摘要

The utility of allenes in metal-catalyzed addition reactions has made these intermediates increasingly popular for an array of synthesis activities. In this context, allenes parallel closely alkynes in their reactivity toward metal-mediated nucleophilic additions. However, unlike alkyne substrates, allenes offer the potential for relaying the associated axial chirality to ensuing bond constructions. For example, allene chirality is faithfully translated to tertiary carbinol stereocenters during Ag(Ⅰ)-catalyzed cyclization of enan-tioenriched allene acetic acid derivatives 1 (eq 1).