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. Author manuscript; available in PMC: 2016 Jun 8.
Published in final edited form as: Angew Chem Int Ed Engl. 2015 Apr 27;54(24):7134–7138. doi: 10.1002/anie.201501505

Scheme 3.

Scheme 3

A) Ruthenium catalyst Ru-4 is required for dihydroxylation. B) Z-4-octene 8 is unreactive in dihydroxylation. C) 8 inhibits the dihydroxylation of 7. Oxidation conditions: NaIO4 (2 eq), CeCl3 (10 mol%), EtOAc:MeCN:H2O (3:3:1), 20 min, 0 °C.