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Pregled bibliografske jedinice broj: 1187421

Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay


Topolovčan, Nikola; Degač, Marina; Čikoš, Ana; Gredičak, Matija
Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay // Journal of organic chemistry, 87 (2022), 3712-3717 doi:10.1021/acs.joc.1c02647 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1187421 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay

Autori
Topolovčan, Nikola ; Degač, Marina ; Čikoš, Ana ; Gredičak, Matija

Izvornik
Journal of organic chemistry (0022-3263) 87 (2022); 3712-3717

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Acid-catalyzed reactions ; Aromatic nucleophiles ; Chemoselective ; Friedel-Crafts alkylation ; Higher yield ; Intramolecular friedel-crafts ; Isoindolinone ; Meyer-Schuster rearrangement ; Propargylic alcohols ; Regioselective synthesis

Sažetak
A Brønsted acid-catalyzed reaction between isoindolinone-derived propargylic alcohols and external aromatic nucleophiles for the construction of spiroisoindolinone indenes is described. The reaction proceeds rapidly with a broad range of substrates to generate spiroindenes chemoselectively and regioselectively in moderate to high yields. Key to the success of this transformation is an intercepted Meyer-Schuster rearrangement/intramolecular Friedel-Crafts alkylation relay that offers a modular approach in the synthesis of target compounds.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
HRZZ-IP-2018-01-4053 - Nove strategije za pripravu tetrasupstituiranih kiralnih centara: asimetrične katalitičke reakcije usmjerene protuanionom (NSYNC-ACDC) (Gredičak, Matija, HRZZ - 2018-01) ( POIROT)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Nikola Topolovčan (autor)

Avatar Url Ana Čikoš (autor)

Avatar Url Matija Gredičak (autor)

Poveznice na cjeloviti tekst rada:

Pristup cjelovitom tekstu rada doi pubs.acs.org doi.org

Citiraj ovu publikaciju:

Topolovčan, Nikola; Degač, Marina; Čikoš, Ana; Gredičak, Matija
Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay // Journal of organic chemistry, 87 (2022), 3712-3717 doi:10.1021/acs.joc.1c02647 (međunarodna recenzija, članak, znanstveni)
Topolovčan, N., Degač, M., Čikoš, A. & Gredičak, M. (2022) Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay. Journal of organic chemistry, 87, 3712-3717 doi:10.1021/acs.joc.1c02647.
@article{article, author = {Topolov\v{c}an, Nikola and Dega\v{c}, Marina and \v{C}iko\v{s}, Ana and Gredi\v{c}ak, Matija}, year = {2022}, pages = {3712-3717}, DOI = {10.1021/acs.joc.1c02647}, keywords = {Acid-catalyzed reactions, Aromatic nucleophiles, Chemoselective, Friedel-Crafts alkylation, Higher yield, Intramolecular friedel-crafts, Isoindolinone, Meyer-Schuster rearrangement, Propargylic alcohols, Regioselective synthesis}, journal = {Journal of organic chemistry}, doi = {10.1021/acs.joc.1c02647}, volume = {87}, issn = {0022-3263}, title = {Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay}, keyword = {Acid-catalyzed reactions, Aromatic nucleophiles, Chemoselective, Friedel-Crafts alkylation, Higher yield, Intramolecular friedel-crafts, Isoindolinone, Meyer-Schuster rearrangement, Propargylic alcohols, Regioselective synthesis} }
@article{article, author = {Topolov\v{c}an, Nikola and Dega\v{c}, Marina and \v{C}iko\v{s}, Ana and Gredi\v{c}ak, Matija}, year = {2022}, pages = {3712-3717}, DOI = {10.1021/acs.joc.1c02647}, keywords = {Acid-catalyzed reactions, Aromatic nucleophiles, Chemoselective, Friedel-Crafts alkylation, Higher yield, Intramolecular friedel-crafts, Isoindolinone, Meyer-Schuster rearrangement, Propargylic alcohols, Regioselective synthesis}, journal = {Journal of organic chemistry}, doi = {10.1021/acs.joc.1c02647}, volume = {87}, issn = {0022-3263}, title = {Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay}, keyword = {Acid-catalyzed reactions, Aromatic nucleophiles, Chemoselective, Friedel-Crafts alkylation, Higher yield, Intramolecular friedel-crafts, Isoindolinone, Meyer-Schuster rearrangement, Propargylic alcohols, Regioselective synthesis} }

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


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