Our group has been developing site-selective C-H bond functionalizations applicable to the derivatization of complex medicinally active synthetic compounds or natural products. This interest has led us to seek catalysts that selectively functionalize hydroxyl groups of polyol natural products by a combination of O-H and C-H bond cleavage to generate ketones by mild transfer dehydrogenation. This lecture will present a catalyst system that oxidizes hindered secondary C-H bonds of complex polyol natural products over more sterically accessible primary C-H bonds and that is sensitive to a combination of steric and electronic properties of the alcohol. Such oxidations enable the incorporation of nitrogen-based functionality into molecules consisting of carbon, hydrogen and oxygen atoms.

Site-Selective oxidation, amination and epimerization reactions of complex polyols enabled by transfer hydrogenation

254th National Meeting (2017)

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