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Polycyclic Indoline-Benzodiazepines through Electrophilic Additions of α-Imino Carbenes to Tröger Bases

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Published in Angewandte Chemie: International Edition. 2018, vol. 57, no. 24, p. 7151-7155
Abstract Polycyclic indoline‐benzodiazepines can be accessed through the intermolecular reaction of Tröger bases with N‐sulfonyl‐1,2,3‐triazoles. Under RhII catalysis, α‐imino carbenes are generated and a subsequent cascade of [1,2]‐Stevens, Friedel–Crafts, Grob, and aminal formation reactions yield the polycyclic heterocycles as single isomers (d.r.>49:1, four stereocenters including two bridgehead N atoms). Further ring expansion by insertion of a second α‐imino carbene leads to elaborated polycyclic 9‐membered‐ring triazonanes.
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Other version: http://doi.wiley.com/10.1002/anie.201803756
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Research group Groupe Lacour
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BOSMANI, Alessandro et al. Polycyclic Indoline-Benzodiazepines through Electrophilic Additions of α-Imino Carbenes to Tröger Bases. In: Angewandte Chemie: International Edition, 2018, vol. 57, n° 24, p. 7151-7155. https://archive-ouverte.unige.ch/unige:105328

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Deposited on : 2018-06-12

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