Journal
ACS CATALYSIS
Volume 6, Issue 6, Pages 3708-3712Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b00846
Keywords
asymmetric cooperative catalysis; photoredox catalysis; organocatalysis; aerobic oxidative olefination; beta-carbolines
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Funding
- NSFC [21072044]
- Henan Province [14IRTSTHN006, 152300410057]
- Czech Science Foundation [13-01061S]
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A cooperative photoredox and asymmetric catalysis for the enantioselective aerobic oxidative C(sp(3))-H olefination of tetrahydro-beta-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 a-substituted THCs and THIQs in high yields with excellent regio- and enantioselectivities (up to 95% ee).
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