The combination of asymmetric hydrogenation of olefins and direct reductive amination

Shuai Yuan, Guorui Gao, Lili Wang, Cungang Liu, Lei Wan, Haizhou Huang (), Huiling Geng () and Mingxin Chang ()
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Shuai Yuan: Northwest A&F University
Guorui Gao: Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Shandong Normal University
Lili Wang: Northwest A&F University
Cungang Liu: Northwest A&F University
Lei Wan: Northwest A&F University
Haizhou Huang: Northwest A&F University
Huiling Geng: Northwest A&F University
Mingxin Chang: Northwest A&F University

Nature Communications, 2020, vol. 11, issue 1, 1-7

Abstract: Abstract Asymmetric hydrogenation (AH) and direct reductive amination (DRA) are both efficient transformations frequently utilized in industry. Here we combine the asymmetric hydrogenation of prochiral olefins and direct reductive amination of aldehydes in one step using hydrogen gas as the common reductant and a rhodium-Segphos complex as the catalyst. With this strategy, the efficiency for the synthesis of the corresponding chiral amino compounds is significantly improved. The practical application of this synthetic approach is demonstrated by the facile synthesis of chiral 3-phenyltetrahydroquinoline and 3-benzylindoline compounds.

Date: 2020
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DOI: 10.1038/s41467-020-14475-x

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