Organic Letters · 2009 · 76 citations · 43 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCatalytic MechanismsDiversity-oriented SynthesisHeterocyclic ChemistryLigand BindingLigand-based DesignOrganic SynthesisLigand DesignPhenylboronic Acid-based Systems
A commercially available 2,3-unsaturated pyranoside, derived from d-glucose, was converted into a new type of olefin phosphorus chelate ligand in only three steps. Application in rhodium catalyzed conjugate additions of phenylboronic acid to enones led to excellent levels of stereoinduction for several cyclic substrates. The easy preparation and the high efficiency of this ligand make it an interesting and promising alternative to established systems.
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Tamio Hayashi, Kazuhito Ueyama, Norihito Tokunaga et al. · Journal of the American Chemical Society · 2003 · 464 citations