Organic Letters · 2009 · 60 citations · 0 references
Natural SciencesChemistryCatalysisOrganic ChemistryCatalytic MechanismsCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisAldehydesAllylic FunctionalizationAsymmetric Heterocycle SynthesisBorylation ReactionsRing-forming ReactionsTransformationsTransition-metal-catalyzed Heterocycle Synthesis
A mild ring opening of vinyl epoxides and aziridines with B(2)Pin(2) catalyzed by Ni(0)-Binap affords new functionalized allylic boron derivatives which undergo sequential transformations. The uncatalyzed allylation of aldehydes allows obtaining challenging bishomoallylic alicyclic 1,3-diols and 1,3-amino alcohols with remarkably high stereoselectivities. Valuable trans-bisallylic 1,4-amino alcohols can be obtained by a simple oxidation.