Pregled bibliografske jedinice broj: 889363
Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles
Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles // Journal of organic chemistry, 82 (2017), 16; 8752-8760 doi:10.1021/acs.joc.7b01420 (međunarodna recenzija, članak, znanstveni)
CROSBI ID: 889363 Za ispravke kontaktirajte CROSBI podršku putem web obrasca
Naslov
Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles
Autori
Glavač, Danijel ; Zheng, Chao ; Dokli, Irena ; You, Shu-Li ; Gredičak, Matija
Izvornik
Journal of organic chemistry (0022-3263) 82
(2017), 16;
8752-8760
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
asymmetric catalysis, chiral Bronsted acid, Friedel-Crafts reaction, quaternary sterecentre
Sažetak
Asymmetric addition of indoles to cyclic α- diaryl-substituted N-acyl imines, which are generated in situ from 3-aryl 3- hydroxyisoindolinones, is described. The transformation proceeds smoothly with a broad range of indoles and isoindolinone alcohols using a SPINOL-derived chiral Brønsted acid catalyst to afford α-tetrasubstituted (3- indolyl)(diaryl)methanamines in excellent yields and enantioselectivities (up to 98% yield, up to >99:1 e.r.). The origin of stereochemical induction is supported by DFT calculations and experimental data.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
Citiraj ovu publikaciju:
Časopis indeksira:
- Current Contents Connect (CCC)
- Web of Science Core Collection (WoSCC)
- Science Citation Index Expanded (SCI-EXP)
- SCI-EXP, SSCI i/ili A&HCI
- Scopus
- MEDLINE
