Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes: development of a metal-free dihydroxylation protocol.

Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol.

The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.

Selective transition-metal-free vicinal cis-dihydroxylation of saturated hydrocarbons.

A transition-metal-free cis-dihydroxylation of saturated hydrocarbons under ambient reaction conditions has been developed. The described approach allows a direct and selective synthesis of vicinal diols. The new reaction thereby proceeds via radical iodination and a sequence of oxidation steps. A broad scope of one-pot dual C(sp3)-H bond functionalization for the selective synthesis of vicinal...

Markedly enhanced recyclability of osmium catalyst in asymmetric dihydroxylation reactions by using macroporous resins bearing both residual vinyl groups and quaternary ammonium moieties.

Markedly enhanced recyclability of osmium catalyst in asymmetric dihydroxylation has been achieved by using osmylated macroporous resins bearing both residual vinyl groups and quaternary ammonium moiety.

Tandem Z - selective cross metathesis – dihydroxylation for the synthesis of anti - 1 , 2 - diols

A stereoselective synthesis of anti-1,2-diols has been developed using a multitasking Ru-catalyst in an assisted tandem catalysis protocol. A cyclometalated ruthenium complex catalyzes first a Zselective cross metathesis of two terminal olefins followed by a stereospecific dihydroxylation. Both steps are catalyzed by Ru, as the Ru-complex is converted to a dihydroxylation catalyst upon addition...

Selective transition-metal-free vicinal cis-dihydroxylation of saturated hydrocarbons† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc03055f Click here for additional data file.