Catalytic hydroamination reactions of olefins are atom-economic and environmentally friendly methods to synthesize chiral amines, a prevalent motif found in large numbers of pharmaceutical agents and agrochemicals. While a variety of catalytic systems have been developed for the Markovnikov reaction, hydroamination in the anti-Markovnikov sense remains one of the most challenging reactions in organic chemistry. Herein, a copper(II)-catalyzed, intermolecular hydroamination of terminal olefins is reported. A series of vinyl arenes have been shown to undergo hydroamination by sulfonamides at catalyst loadings as low as 5 mol%, yielding exclusively the anti-Markovnikov product. The use of chiral ligands for asymmetric induction in the hydroamination of α-substituted vinyl arene substrates has also been examined.

Copper-catalyzed, intermolecular, anti-Markovnikov hydroamination of olefins

2019 Spring National Meeting

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