1610930-72-7Relevant articles and documents
Phase-transfer-catalysed synthesis of pyrroloindolines and pyridoindolines by a hydrogen-bond-assisted isocyanide cyclization cascade
Knipe, Peter C.,Gredicak, Matija,Cernijenko, Artiom,Paton, Robert S.,Smith, Martin D.
, p. 3005 - 3009 (2014)
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. Generating complexity: A cascade reaction that generates pyrrolo- and pyridoindoline motifs from isocyanide precursors under phase-transfer conditions is described. 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 (see scheme).
