Chemoselective Strategy for the Direct Formation of Tetrahydro-2,5-methanobenzo[c]azepines or Azetotetrahydroisoquinolines via Regio- and Stereoselective Reactions
journal contributionposted on 14.05.2019, 00:00 by Ervin Kovács, Balázs Huszka, Tamás Gáti, Miklós Nyerges, Ferenc Faigl, Zoltán Mucsi
The present study reports regio- and highly diastereoselective preparative methods for the synthesis of versatile alkaloid-type compounds from oxiranylmethyl tetrahydroisoquinolines. 2,5-Methanobenzo[c]azepines or azetidine-fused heterocycles were synthesized in tandem reactions depending on the absence or presence of a BF3 co-reagent. A high functional group tolerance has also been demonstrated. DFT calculations with an explicit solvent model confirmed the proposed reaction mechanisms and the role of kinetic controls on the stereochemical outcome of the reported new methods.
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diastereoselectivetandem reactionsStereoselective ReactionsAzetotetrahydroisoquinolinestereochemical outcomestudy reports regioazetidine-fused heterocyclesreaction mechanismsTetrahydroMethanobenzopresencealkaloid-type compoundsabsenceRegiooxiranylmethyl tetrahydroisoquinolinesmethodDirect FormationsynthesisDFT calculationsBF 3 co-reagentazepineroleChemoselective Strategygroup tolerancemodel