One-Pot Enantioselective Synthesis of 2‑Pyrrolidinone Derivatives Bearing a Trifluoromethylated All-Carbon Quaternary Stereocenter
A new methodology for the one-pot enantioselective construction of 2-pyrrolidinone derivatives bearing a trifluoromethylated all-carbon quaternary stereocenter at the 4-position has been described. This strategy combines an organocatalytic conjugate addition of nitroalkanes to isatin-derived α-trifl...
Gespeichert in:
Veröffentlicht in: | Organic letters 2019-12, Vol.21 (23), p.9584-9588 |
---|---|
Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | A new methodology for the one-pot enantioselective construction of 2-pyrrolidinone derivatives bearing a trifluoromethylated all-carbon quaternary stereocenter at the 4-position has been described. This strategy combines an organocatalytic conjugate addition of nitroalkanes to isatin-derived α-trifluoromethyl acrylates and a reduction/lactamization process, affording the corresponding products in moderate to high yields (50–95%) with generally excellent stereoselectivities (up to 96% ee and >20:1 dr). |
---|---|
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.9b03758 |