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RESEARCH PRODUCT
Asymmetric Synthesis of Spirobenzazepinones with Atroposelectivity and Spiro-1,2-Diazepinones by NHC-Catalyzed [3+4] Annulation Reactions
Rakesh PuttreddyLei WangMarcus BlümelAi WangSun LiArne R. PhilippsKari RissanenDieter Enderssubject
chemistry.chemical_classificationAnnulationSpiro compound010405 organic chemistryStereochemistry2-diazepinone1asymmetric synthesisEnantioselective synthesisGeneral MedicineGeneral Chemistrybenzazepinonespiro compound010402 general chemistry01 natural sciencesCatalysis0104 chemical sciencesStereocenterCatalysischemistry.chemical_compoundchemistryMoietyOxindoleta116N-heterocyclic carbenedescription
A strategy for the NHC-catalyzed asymmetric synthesis of spirobenzazepinones, spiro-1,2-diazepinones, and spiro-1,2-oxazepinones has been developed via [3+4]-cycloaddition reactions of isatin-derived enals (3C component) with in-situ-generated aza-o-quinone methides, azoalkenes, and nitrosoalkenes (4atom components). The [3+4] annulation strategy leads to the seven-membered target spiro heterocycles bearing an oxindole moiety in high yields and excellent enantioselectivities with a wide variety of substrates. Notably, the benzazepinone synthesis is atroposelective and an all-carbon spiro stereocenter is generated.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-07-20 | Angewandte Chemie International Edition |