Get access

OsO4⋅Streptavidin: A Tunable Hybrid Catalyst for the Enantioselective cis-Dihydroxylation of Olefins

Authors


  • We thank Prof. C. R. Cantor for the SAV gene, Chiral Technologies Europe for help with the method development for chiral-phase HPLC analysis, Beat Amrein for preliminary experiments, and Maurus Schmid for his contribution to the artwork. This research was funded by the Swiss National Science Foundation (Grant 200020-126366), the Cantons of Basel, and the Marie Curie Training Network (FP7-ITN-238434).

Abstract

original image

Taking control: Selective catalysts for olefin dihydroxylation have been generated by the combination of apo-streptavidin and OsO4. Site-directed mutagenesis allows improvement of enantioselectivity and even inversion of enantiopreference in certain cases. Notably allyl phenyl sulfide and cis-β-methylstyrene were converted with unprecedented enantiomeric excess.

Ancillary