Polycyclic Indoline‐Benzodiazepines through Electrophilic Additions of α‐Imino Carbenes to Tröger Bases |
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| Authors: | Alessandro Bosmani Alejandro Guarnieri‐Ibáñez Dr Sébastien Goudedranche Dr Céline Besnard Prof Jérôme Lacour |
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| Institution: | 1. http://www.unige.ch/sciences/chiorg/lacour/;2. Département de Chimie Organique, Université de Genève, Geneva 4, Switzerland;3. Laboratoire de Cristallographie, Université de Genève, Geneva 4, Switzerland |
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| 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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| Keywords: | benzodiazepines cascade reactions indolines rhodium α -imino carbenes |
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