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A General and Expeditious One-Pot Synthesis of Sulfoxides in High Optical Purity from Norephedrine-Derived Sulfamidites
51
Citations
24
References
2002
Year
Bioorganic ChemistryEngineeringSynthetic PhotochemistryOrganic ChemistryChemistryDesulfurizationChemical EngineeringMedicinal ChemistryNorephedrine-derived N-benzyloxycarbonylsulfamidite 3AHigh Optical PurityStereoselective SynthesisSulfoxides 6Expeditious One-pot SynthesisCatalysisPharmacologyAsymmetric CatalysisEnantioselective SynthesisNatural SciencesSimple ProcedureSynthetic ChemistryNorephedrine-derived Sulfamidites
A general and simple procedure for preparing any kind of enantiomerically enriched sulfoxide starting from norephedrine-derived N-benzyloxycarbonylsulfamidite 3a is reported. After one-pot reaction of 3a with RMgX, HBF(4), and R'MgX, a variety of sulfoxides 6 are obtained in ee usually higher than 93% and isolated yields ranging between 50 and 78%. The obtained configuration is tunable by simply electing the order of the addition of the reagents. [reaction--see text]
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