Asymmetric a-alkylation of enantiopure 1,1'-binaphthalene-2,2'-diol (BINOL) derivatives of benzylphosphonic acid provides diastereoenriched products. Facile separation of diastereomers via column chromatography followed by cleavage of the chiral auxiliary yields the corresponding optically pure phosphonic acids. Subsequent treatment of these chiral phosphonic (and diphosphonic) acids with an appropriate vanadium precursor under solvothermal conditions affords molecular and non-molecular vanadium phosphonates. Such materials were shown to exhibit exemplary catalytic activity for the epoxidation of a variety of alkene substrates in the presence of tBuOOH. Yields and extent of asymmetric induction will be discussed.

Chiral vanadium phosphonates: Synthesis, characterization, and applications to heterogeneous asymmetric epoxidation

246th National Meeting (2013)

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