Gold(I)-Catalyzed One-Pot and Diastereoselective Synthesis of <i>trans</i>-2-Silyl-4,5-dihydrofurans from Propargylsilanes and Aldehydes
Sergio Fernández, Javier Santamarı́a, Alfredo Ballesteros
Abstract
A diastereoselective and high-yielding gold-catalyzed synthesis of trans-2-silyl-4,5-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.
Topics & Concepts
ChemistryIsomerizationIntramolecular forceSilylationCatalysisRing (chemistry)Combinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalytic Alkyne ReactionsPhytochemical compounds biological activitiesSynthetic Organic Chemistry Methods