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Pregled bibliografske jedinice broj: 889363

Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles


Glavač, Danijel; Zheng, Chao; Dokli, Irena; You, Shu-Li; Gredičak, Matija
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)


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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



POVEZANOST RADA


Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Matija Gredičak (autor)

Avatar Url Irena Dokli (autor)

Avatar Url Danijel Glavač (autor)

Citiraj ovu publikaciju

Glavač, Danijel; Zheng, Chao; Dokli, Irena; You, Shu-Li; Gredičak, Matija
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)
Glavač, D., Zheng, C., Dokli, I., You, S. & Gredičak, M. (2017) Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles. Journal of organic chemistry, 82 (16), 8752-8760 doi:10.1021/acs.joc.7b01420.
@article{article, year = {2017}, pages = {8752-8760}, DOI = {10.1021/acs.joc.7b01420}, keywords = {asymmetric catalysis, chiral Bronsted acid, Friedel-Crafts reaction, quaternary sterecentre}, journal = {Journal of organic chemistry}, doi = {10.1021/acs.joc.7b01420}, volume = {82}, number = {16}, issn = {0022-3263}, title = {Chiral Br\onsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles}, keyword = {asymmetric catalysis, chiral Bronsted acid, Friedel-Crafts reaction, quaternary sterecentre} }
@article{article, year = {2017}, pages = {8752-8760}, DOI = {10.1021/acs.joc.7b01420}, keywords = {asymmetric catalysis, chiral Bronsted acid, Friedel-Crafts reaction, quaternary sterecentre}, journal = {Journal of organic chemistry}, doi = {10.1021/acs.joc.7b01420}, volume = {82}, number = {16}, issn = {0022-3263}, title = {Chiral Br\onsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles}, keyword = {asymmetric catalysis, chiral Bronsted acid, Friedel-Crafts reaction, quaternary sterecentre} }

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


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