6533b834fe1ef96bd129d5a9
RESEARCH PRODUCT
Asymmetric Synthesis of Spirocyclic β-Lactams through Copper-Catalyzed Kinugasa/Michael Domino Reactions
Carolina Von EssenSun LiDieter EndersKari RissanenTao ShuLong ZhaoXiang-yu Chensubject
Molecular Structure010405 organic chemistryStereochemistryChemistryasymmetric synthesisEnantioselective synthesisGeneral MedicineGeneral Chemistrybeta-Lactams010402 general chemistry01 natural sciencesDesymmetrizationCatalysisDomino0104 chemical sciencesCatalysisStereocenterCascade reactionAlkynesβ lactamsStereoselectivityta116Copperdescription
The first copper-catalyzed highly chemo-, regio-, diastereo-, and enantioselective Kinugasa/Michael domino reaction for the desymmetrization of prochiral cyclohexadienones is described. In the presence of a chiral copper catalyst, alkyne-tethered cyclohexadienones couple with nitrones to generate the chiral spirocyclic lactams with excellent stereoselectivity (up to 97 % ee, >20:1 dr). The new method provides direct access to versatile highly functionalized spirocyclic β-lactams possessing four contiguous stereocenters, including one quaternary and one tetra-substituted stereocenter.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2018-07-18 | Angewandte Chemie International Edition |