Journal
ORGANIC LETTERS
Volume 22, Issue 16, Pages 6590-6594Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02356
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Funding
- Spanish Government MINECO/FEDER [CTQ-2016-76840-R]
- MINECO [FPU2016-07221]
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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.
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