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Catalytic asymmetric hydroamination of unactivated internal olefins to aliphatic amines

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Science  03 Jul 2015:
Vol. 349, Issue 6243, pp. 62-66
DOI: 10.1126/science.aab3753

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Elaborate amines from commodity olefins

Fine spatial control over the formation of carbon-nitrogen bonds is essential to the synthesis of many pharmaceutical and agrochemical compounds. Yang et al. synthesized a copper catalyst that shows exceptional discrimination between similar substituents in the addition of N-H bonds across the C-C double bonds of simple olefins. In particular, the catalyst favors one of two mirror-image products that differ in the relative orientations of methyl and ethyl groups. This selectivity fosters the use of readily available commodity olefins in the preparation of complex chiral amines.

Science, this issue p. 62

Abstract

Catalytic assembly of enantiopure aliphatic amines from abundant and readily available precursors has long been recognized as a paramount challenge in synthetic chemistry. Here, we describe a mild and general copper-catalyzed hydroamination that effectively converts unactivated internal olefins—an important yet unexploited class of abundant feedstock chemicals—into highly enantioenriched α-branched amines (≥96% enantiomeric excess) featuring two minimally differentiated aliphatic substituents. This method provides a powerful means to access a broad range of advanced, highly functionalized enantioenriched amines of interest in pharmaceutical research and other areas.

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