Asymmetric Allylic C-H Oxidation for the Synthesis of Chromans.

Pu-Sheng Wang, Peng Liu, Yu-Jia Zhai, Hua-Chen Lin, Zhi-Yong Han, Liu-Zhu Gong

Journal of the American Chemical Society 2015 Oct 14

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An enantioselective intramolecular allylic C-H oxidation to generate optically active chromans has been accomplished under the cooperative catalysis of a palladium complex of chiral phosphoramidite ligand and 2-fluorobenzoic acid. Mechanistic studies suggest that this reaction commences with a Pd-catalyzed allylic C-H activation event and then undergoes asymmetric allylic alkoxylation. The synthetic significance of the method has been embodied by concisely building up a key chiral intermediate to access (+)-diversonol.

Citation

Pu-Sheng Wang, Peng Liu, Yu-Jia Zhai, Hua-Chen Lin, Zhi-Yong Han, Liu-Zhu Gong. Asymmetric Allylic C-H Oxidation for the Synthesis of Chromans. Journal of the American Chemical Society. 2015 Oct 14;137(40):12732-5