6533b830fe1ef96bd12971d1
RESEARCH PRODUCT
Enantioselective Synthesis of Pyrrolizidinone Scaffolds through Multiple-Relay Catalysis
María Sánchez-rosellóCarlos Del PozoFernando Rabasa-alcañizJavier Torres FernándezMarcos Escolanosubject
Tandem010405 organic chemistryOrganic ChemistryEnantioselective synthesisSequence (biology)Conjugated system010402 general chemistry01 natural sciencesBiochemistryCombinatorial chemistry0104 chemical sciencesCatalysisStereocenterchemistry.chemical_compoundchemistryMichael reactionPhysical and Theoretical ChemistryPhosphoric aciddescription
A triple-tandem protocol for the synthesis of the pyrrolizidinone skeleton has been devised. It involves a cross metathesis-intramolecular aza-Michael reaction-intramolecular Michael addition tandem sequence, starting from N-pentenyl-4-oxo-2-alkenamides and conjugated ketones. In the presence of two cooperative catalysts, namely the second-generation Hoveyda-Grubbs catalyst and (R)-TRIP-derived BINOL phosphoric acid, this multiple-relay catalytic process takes place in good yields and outstanding levels of diastero- and enantioselectivity with the simultaneous generation of three contiguous stereocenters.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-12-01 | Organic Letters |