Organic Letters · 2007 · 16 citations · 2 references
Natural SciencesChemistryMedicinal ChemistryGreen ChemistryOrganometallic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsAsymmetric Heterocycle SynthesisDesymmetrization By ReductionEnantioselective SynthesisKetonesMedicinal HeterocyclesOxygen HeterocyclesStereoselective Synthesis
The stereoselective synthesis of tetrasubstituted tetrahydrofurans and trisubstituted tetrahydropyrans bearing a sulfoxide was achieved by reductive cyclization (Et3SiH/TMSOTf) from the corresponding enantiopure hydroxy ketones protected as a dioxolane. These derivatives are easily accessible from a Reformatsky-type reaction between alpha-bromo-alpha'-sulfinyl ketones and protected alpha- or beta-ketoaldehydes, followed by diastereoselective reduction of the resulting beta-ketosulfoxide.
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Michel Obringer, Françoise Colobert, Benjamin Neugnot et al. · Organic Letters · 2003 · 32 citations