Organic Letters · 2017 · 27 citations · 36 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalytic MechanismsOrganometallic SynthesisAlkylation ReactionsAllylic FunctionalizationHeck ReactionPalladium Catalysts
The selective palladium-catalyzed carboamination of allylic alcohols is reported on the basis of the use of an easily introduced trifluoroacetaldehyde-derived tether. Aminoalkynylation reactions were realized using alkynyl bromides and commercially available phosphine ligands. For aminoarylations, a new biaryl phosphine ligand, "Fu-XPhos", was introduced to overcome a competitive Heck pathway. The carboamination products were obtained in high yields and diastereoselectivity. The tether could be easily removed to give value-added amino alcohol building blocks.
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The Synthesis of Vicinal Amino Alcohols
Stephen C. Bergmeier · Tetrahedron · 2000 · 912 citations
Guosheng Liu, Shannon S. Stahl · Journal of the American Chemical Society · 2006 · 415 citations