OsO4⋅Streptavidin: A Tunable Hybrid Catalyst for the Enantioselective cis-Dihydroxylation of Olefins†
Dr. Valentin Köhler
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
These authors contributed equally to this work.
Search for more papers by this authorDr. Jincheng Mao
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
These authors contributed equally to this work.
Search for more papers by this authorTillmann Heinisch
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Biozentrum, Universität Basel, Klingelbergstrasse 50/70, 4056 Basel (Switzerland)
These authors contributed equally to this work.
Search for more papers by this authorDr. Anca Pordea
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorDr. Alessia Sardo
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorDr. Yvonne M. Wilson
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorLivia Knörr
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorDr. Marc Creus
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorJean-Christophe Prost
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorCorresponding Author
Prof. Dr. Tilman Schirmer
Biozentrum, Universität Basel, Klingelbergstrasse 50/70, 4056 Basel (Switzerland)
Tilman Schirmer, Biozentrum, Universität Basel, Klingelbergstrasse 50/70, 4056 Basel (Switzerland)
Thomas R. Ward, Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorCorresponding Author
Prof. Dr. Thomas R. Ward
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Tilman Schirmer, Biozentrum, Universität Basel, Klingelbergstrasse 50/70, 4056 Basel (Switzerland)
Thomas R. Ward, Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorDr. Valentin Köhler
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
These authors contributed equally to this work.
Search for more papers by this authorDr. Jincheng Mao
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
These authors contributed equally to this work.
Search for more papers by this authorTillmann Heinisch
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Biozentrum, Universität Basel, Klingelbergstrasse 50/70, 4056 Basel (Switzerland)
These authors contributed equally to this work.
Search for more papers by this authorDr. Anca Pordea
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorDr. Alessia Sardo
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorDr. Yvonne M. Wilson
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorLivia Knörr
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorDr. Marc Creus
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorJean-Christophe Prost
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorCorresponding Author
Prof. Dr. Tilman Schirmer
Biozentrum, Universität Basel, Klingelbergstrasse 50/70, 4056 Basel (Switzerland)
Tilman Schirmer, Biozentrum, Universität Basel, Klingelbergstrasse 50/70, 4056 Basel (Switzerland)
Thomas R. Ward, Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorCorresponding Author
Prof. Dr. Thomas R. Ward
Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Tilman Schirmer, Biozentrum, Universität Basel, Klingelbergstrasse 50/70, 4056 Basel (Switzerland)
Thomas R. Ward, Departement Chemie, Universität Basel, Spitalstrasse 51, 4056 Basel (Switzerland)
Search for more papers by this authorWe 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).
Graphical Abstract
Gut kombiniert: Die Kombination von Apostreptavidin mit OsO4 lieferte selektive Katalysatoren für die Olefindihydroxylierung. Durch ortsgerichtete Mutagenese gelang eine Verbesserung der Enantioselektivität und in bestimmten Fällen sogar eine Umkehr der Enantiopräferenz. Vor allem Allylphenylsulfid und cis-β-Methylstyrol wurden mit bislang unerreichtem Enantiomerenüberschuss umgesetzt.
Supporting Information
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