New platinum-catalysed dihydroalkoxylation of allenes

Munoz-Herranz, Maria and de la Torre, María C. and Sierra, Miguel A. (2010) New platinum-catalysed dihydroalkoxylation of allenes. Advanced Synthesis & Catalysis, 352 (13). pp. 2189-2194. ISSN 1615-4150

Abstract

A new platinum-catalysed dihydroalkoxylation of allenes is described to give aliphatic acetals by an unexpected attack of two molecules of methanol to the terminal carbon of the allene moiety. Deuteration experiments suggest an unprecedented formal 1,3-dipolar addition of methanol to a zwitterionic platinum carbene as the key step. The first platinum-catalysed intermolecular carbon-based nucleophile addition to allenes is also reported.