Cyclopropyl rings are a pervasive motif in a multitude of biologically-active molecules including drug targets and pharmateuticals. Alkylidenecyclopropanes (ACPs) present themselves as logical substrates for the installation of cyclopropyl rings into organic molecules due to their strain-driven reactivity and ease of synthesis. While ACPs have been widely employed in organic synthesis, transistion-metal catalyzed functionalizations typically result in cyclopropyl C-C bond cleavage with few exceptions. Herein, our studies leading to the development of a highly regio- and diastereo- selective gold(I)-catalyzed anti-Markovnikov hydroamination of ACPs with a variety of nucleophiles will be presented. Importantly, this transoformation proceeds without cyclopropyl ring opening. Additionally, our development of a gold(I)-catalyzed anti-Markovnikov hydroarylation of ACPs with indoles will be presented and experimentally founded mechanistic investigations on the aforementioned transformations will be discussed.

Gold(I)-catalyzed anti-Markovnikov hydrofunctionalization reactions of alkylidenecyclopropanes

251st National Meeting (2016)

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