The combination of asymmetric hydrogenation of olefins and direct reductive amination

• Published in: Nature communications Vol. 11; no. 1; p. 621
• Main Authors: Yuan, Shuai, Gao, Guorui, Wang, Lili, Liu, Cungang, Wan, Lei, Huang, Haizhou, Geng, Huiling, Chang, Mingxin
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 30.01.2020; Nature Publishing Group; Nature Portfolio
• Subjects: 140/131; 140/58; 639/638/403/933; 639/638/403/935; 639/638/77/883; 639/638/77/888; Aldehydes; Alkenes; Amination; Asymmetry; Catalysts; Chemical industry; Direct reduction; Humanities and Social Sciences; Hydrogen storage; Hydrogenation; multidisciplinary; Organic chemistry; Rhodium; Science; Science (multidisciplinary)
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/s41467-020-14475-x

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. Asymmetric hydrogenation (AH) and direct reductive amination (DRA) are both frequently utilized in chemical industry. Here, the authors combine these two transformations to efficiently convert in one step prochiral olefins into chiral amino compounds.