Organoboron compounds are among the most useful organic compounds in organic synthesis. Organoboranes can be oxidised to alcohols by several oxidants, such as hydroperoxides or peroxides. In this work, we investigated the application of the chiral hydroperoxide TADOOH (1 ) in the oxidation of organoboranes, aiming their oxidative kinetic resolution (Scheme 1). After screening studies for the enantioselective oxidation, the use of -30 oC, 1 equivalent of NaOH, 0.5 equivalent of oxidant (TADOOH) showed promising results. For example, the oxidation of organoborane 2b  gave the alcohol 3b  with 40% e.e. in 20% conversion. These results showed us that the use of chiral hydroperoxide to perform a kinetic resolution of organoboranes can be achieved.Scheme 1: Oxidation of organoboranes with TADOOH.

Studies about oxidative kinetic resolution of organoboranes by chiral hydroperoxides

248th National Meeting (2014)

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