Site-selective C–H functionalization is a major challenge in organic synthesis. This research will show the subtle influences of catalysts and protecting groups on controlling the site-selectivity of C–H functionalization by rhodium-carbene intermediates. The reference system used in the study is piperidine derivatives and generated derivatives of methylphenidate in one pot. The key step is the dirhodium-catalyzed C–H insertion reaction of donor/acceptor carbenes. By modifying the structure of the dirhodium catalyst and the nature of piperidine unsaturation and/or the nitrogen protecting group, C–H functionalization can be achieved at either C2, C3 or C4 of the piperidine ring.

Site- and stereoselective functionalization of piperidine derivatives

2019 Spring National Meeting

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