Enantioselective Aerobic Oxidative C(sp3)–H Olefination of Amines via Cooperative Photoredox and Asymmetric Catalysis

A cooperative photoredox and asymmetric catalysis for the enantioselective aerobic oxidative C­(sp3)–H olefination of tetrahydro-β-carbolines (THCs) is reported. This method, which is also effective for tetrahydroisoquinolines (THIQs), features a triple-catalyst strategy, involving a dicyanopyrazine...

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Bibliographic Details
Published inACS catalysis Vol. 6; no. 6; pp. 3708 - 3712
Main Authors Wei, Guo, Zhang, Chenhao, Bureš, Filip, Ye, Xinyi, Tan, Choon-Hong, Jiang, Zhiyong
Format Journal Article
LanguageEnglish
Published American Chemical Society 03.06.2016
Subjects
organocatalysis
photoredox catalysis
β-carbolines
asymmetric cooperative catalysis
aerobic oxidative olefination
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Summary:A cooperative photoredox and asymmetric catalysis for the enantioselective aerobic oxidative C­(sp3)–H olefination of tetrahydro-β-carbolines (THCs) is reported. This method, which is also effective for tetrahydroisoquinolines (THIQs), features a triple-catalyst strategy, involving a dicyanopyrazine-derived chromophore (DPZ) as the metal-free photoredox catalyst, a chiral Lewis base catalyst, and an inorganic salt cocatalyst. The current protocol provides straightforward access to a series of valuable α-substituted THCs and THIQs in high yields with excellent regio- and enantioselectivities (up to 95% ee).
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.6b00846