H-Bond Donor-Directed Switch of Diastereoselectivity in the Enantioselective Intramolecular Aza-Henry Reaction of Ketimines.
Chemistry
; : e202402488, 2024 Aug 09.
Article
in En
| MEDLINE
| ID: mdl-39120485
ABSTRACT
We report an H-bond donor controlled diastereoselective switchable intramolecular aza-Henry reaction of ketimines derived from α-ketoesters and 2-(2-nitroethyl)anilines, allowing facile access to chiral tetrahydroquinolines bearing an aza-quaternary carbon stereocenter, which are privileged scaffold for medicinal researches. While newly developed cinchona alkaloid derived phosphoramide-bearing quaternary ammonium salt C2 selectively give cis-adducts in up to 201 dr and 99% ee, the corresponding urea-bearing analogue C8 preferentially give trans-adducts in up to 201 dr and 99% ee.
Full text:
1
Database:
MEDLINE
Language:
En
Journal:
Chemistry
Journal subject:
QUIMICA
Year:
2024
Type:
Article
Affiliation country:
China