Abstract
Different primary benzyl-type carbamates were deprotonated by sec-butyllithium in the presence of a tert-leucinol-derived bis(oxazoline) ligand. The resulting configurationally labile epimeric complexes equilibrated and one diastereomer was strongly favored in the equilibria. After dynamic thermodynamic resolution, the complexes could be trapped with different classes of electrophiles to yield highly enantioenriched secondary benzyl carbamates. The stereochemical course of the substitution reactions was elucidated. High-level quantum chemical investigations were performed and allowed a prediction of both the favored complex and the enantiomeric excess that could be expected within the reactions.
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