Mostrar el registro sencillo del ítem
Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement
dc.contributor.author | Sathish, Manda | |
dc.contributor.author | Nachtigall, Fabiane Manke | |
dc.contributor.author | Santos, Leonardo S. | |
dc.date.accessioned | 2020-11-10T17:09:14Z | |
dc.date.available | 2020-11-10T17:09:14Z | |
dc.date.issued | 2020-10-21 | |
dc.identifier | 10.1039/d0ra07705d | |
dc.identifier.issn | 20462069 | |
dc.identifier.uri | https://hdl.handle.net/20.500.12728/7163 | |
dc.description.abstract | Tetrahydro-β-carboline (THBC) is a tricyclic ring system that can be found in a large number of bioactive alkaloids. Herein, we report a simple and efficient method for the synthesis of enantiopure THBCs through a chiral thiosquaramide (11b) catalyzed imine reduction of dihydro-β-carbolines (17a-f). The in situ generated Pd-H employed as hydride source in the reaction of differently substituted chiral THBCs (18a-f) afforded high selectivities (R isomers, up to 96% ee) and good isolated yields (up to 88%). Moreover, the chiral thiosquaramide used also afforded exceptional catalyst activity in the syntheses of (-)-coerulescine (5) and (-)-horsfiline (6) with excellent enantioselectivities up to 98% and 93% ee, respectively, via an enantioselective oxidative rearrangement approach. | es_ES |
dc.language.iso | en | es_ES |
dc.publisher | Royal Society of Chemistry | es_ES |
dc.subject | Catalysis | es_ES |
dc.subject | Catalyst activity | es_ES |
dc.subject | Enantioselectivity | es_ES |
dc.subject | Isomers | es_ES |
dc.subject | Pyridine | es_ES |
dc.title | Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement | es_ES |
dc.type | Article | es_ES |