Gold(I)-Catalyzed One-Pot and Diastereoselective Synthesis of trans-2-Silyl-4,5-dihydrofurans from Propargylsilanes and Aldehydes

A diastereoselective and high-yielding gold-catalyzed synthesis of trans-2-silyl-4,S-dihydrofurans is described. In addition to a sequential manner, this reaction could be performed in a one-pot procedure from propargylsilanes and aldehydes. A mechanistic proposal for the cis-trans isomerization step is formulated. To provide experimental support for this proposal, which involves ring opening/ring closing steps of the dihydrofuran, several isotopically labeled experiments, intramolecular capture of a proposed intermediate, and construction of a Hammett plot have been performed.