Naslov
Phase-Transfer-Catalysed Synthesis of Pyrroloindolines and Pyridoindolines by a Hydrogen-Bond-Assisted Isocyanide Cyclization Cascade

Autori
Knipe, Peter C. ; Gredičak, Matija ; Cernijenko, Artiom ; Paton, Robert S. ; Smith, Martin D.

Izvornik
Chemistry : a European journal (0947-6539) 20 (2014), 11; 3005-3009

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

Ključne riječi
density functional calculations; cascade reactions; heterocycles; hydrogen bonds; isocyanides; phase-transfer catalysis

Sažetak
A cascade reaction that generates pyrrolo- and pyridoindoline motifs from isocyanide precursors under phase-transfer conditions is described. This transformation proceeds at room temperature in the presence of a quaternary ammonium catalyst and base to generate functionalized products containing an all-carbon quaternary stereocentre. Quantum chemical calculations demonstrated that intramolecular general acid catalysis plays a key accelerating role through stabilization of developing charge in the transition state, and that the reaction is best described as a 5-endo dig cyclization, rather than an anionic 6π electrocyclization. Investigations employing chiral phase-transfer catalysts have given promising selectivities to date.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA