6533b7d4fe1ef96bd12633b7
RESEARCH PRODUCT
Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives.
Qiang LiuSun LiKari RissanenXiang-yu ChenJiawen XiongHe ShengDieter EndersCarolina Von Essensubject
StereochemistrySubstituent010402 general chemistry01 natural sciencesCatalysisStereocenterCatalysischemistry.chemical_compoundaldehyditaldehydesPhenyl groupOxindoleta116orgaaniset yhdisteetkemiallinen synteesi010405 organic chemistryEnantioselective synthesisGeneral MedicineGeneral ChemistryCycloaddition0104 chemical scienceschemistryorganic compoundsCarbenechemical synthesisdescription
A strategy to control the switch between a non‐cycloaddition reaction and a cycloaddition reaction of enals, using N‐heterocyclic carbene (NHC) catalyisis, has been developed. The new scalable protocol leads to γ‐amino‐acid esters bearing a tetrasubstituted stereocenter in good yields and high stereoselectivities by homo‐Mannich reactions of enals and isatin‐derived ketimines. By simply changing the N‐ketimine substituent to an ortho‐hydroxy phenyl group, the corresponding spirocyclic oxindolo‐γ‐lactams are obtained. peerReviewed
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-12-05 | Angewandte Chemie (International ed. in English) |