Chiral-Boron-Complex Catalyzed Asymmetric Inverse-Electron-Demand Aza-Diels-Alder Reaction of ß-Trifluoromethyl α,ß-Unsaturated Ketones with Cyclic N-Sulfonyl Ketimines.
Org Lett
; 25(38): 6982-6986, 2023 Sep 29.
Article
in En
| MEDLINE
| ID: mdl-37721381
ABSTRACT
A highly efficient asymmetric inverse-electron-demand aza-Diels-Alder reaction of ß-trifluoromethyl α,ß-unsaturated ketone with cyclic N-sulfonyl ketimines catalyzed by (R)-3,3'-I2-BINOL-boron-complex was developed. A broad range of fused piperidine derivatives bearing stereogenic carbon containing CF3 motifs were prepared in high yields with excellent diastereo- and enantioselectivities (up to >201 dr, and >99% ee). This protocol had the characteristics of mild reaction conditions, high efficiency, and high stereoselectivity.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2023
Document type:
Article
Affiliation country: