Enantioselective Synthesis of Pyrrolizidinone Scaffolds through Multiple-Relay Catalysis
| Autor: | María Sánchez-Roselló, Carlos del Pozo, Fernando Rabasa-Alcañiz, Javier Torres Fernández, Marcos Escolano |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Tandem
010405 organic chemistry Organic Chemistry Enantioselective synthesis Sequence (biology) Conjugated system 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis Stereocenter chemistry.chemical_compound chemistry Michael reaction Physical and Theoretical Chemistry Phosphoric acid |
| Zdroj: | Organic Letters. 22:9433-9438 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.0c03344 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|