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Realizing an Aza Paternò–Büchi Reaction
Author(s) -
Kumarasamy Elango,
Kandappa Sunil Kumar,
Raghunathan Ramya,
Jockusch Steffen,
Sivaguru Jayaraman
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201702273
Subject(s) - isomerization , imine , chemistry , azetidine , yield (engineering) , intramolecular force , reactivity (psychology) , selectivity , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , materials science , medicine , alternative medicine , pathology , metallurgy
Intramolecular atropselective aza Paternò–Büchi reaction involving atropisomeric enamide and imine functionalities under sensitized irradiation leads to azetidine products in good yield and selectivity ( ee >96 %). A mechanistic model based on detailed photophysical and isomerization kinetic studies is provided that shed light into the reactivity of enamides leading to aza Paternò–Büchi reaction.