6533b7d3fe1ef96bd12608bd
RESEARCH PRODUCT
Thiourea-Catalyzed Domino Michael–Mannich [3+2] Cycloadditions: A Strategy for the Asymmetric Synthesis of 3,3′-Pyrrolidinyl-dispirooxindoles
Kari RissanenDieter EndersCarolina Von EssenKun ZhaoYing Zhisubject
010405 organic chemistryStereochemistryIsatinOrganic ChemistryEnantioselective synthesis010402 general chemistry01 natural sciencesCombinatorial chemistryCycloadditionDomino0104 chemical sciencesStereocenterchemistry.chemical_compoundchemistryCascade reactionThioureaOrganocatalysisdescription
The asymmetric synthesis of trifluoromethylated 3,3′-pyrrolidinyl-dispirooxindole derivatives with four contiguous stereogenic centers, including two vicinal spiro-stereocenters, is described. Employing a bifunctional thiourea catalyst, a domino Michael–Mannich [3+2] cycloaddition occurs readily between isatin ketimines and isatin-derived enoates with good yields and very high stereoselectivities, providing a direct entry to the title compounds of potential medical value.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-07-13 | Synlett |