Organic Letters · 2012 · 22 citations · 48 references
Natural SciencesChemistryMedicinal ChemistryBioorganic ChemistryOrganic ChemistrySynthetic Medicinal ChemistryAddition ReactionsHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisConjugate AdditionHeterocyclic Ring OpeningRing-forming ReactionsStereoselective C-h FunctionalizationStereospecific Reactions
A new stereoselective tandem reaction consisting of the metal-free conjugate addition of boronic acids followed by an intramolecular ring opening of a cyclic acetal has been disclosed. Optically pure polysubstituted tetrahydropyrans have been synthesized diastereoselectively by this new reaction. Two new C-C bonds and up to three stereocenters are formed in a single step, allowing the generation of quaternary stereocenters.
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