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Polycyclic Indoline‐Benzodiazepines through Electrophilic Additions of α‐Imino Carbenes to Tröger Bases
Author(s) -
Bosmani Alessandro,
GuarnieriIbáñez Alejandro,
Goudedranche Sébastien,
Besnard Céline,
Lacour Jérôme
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201803756
Subject(s) - stereocenter , aminal , indoline , chemistry , carbene , ring (chemistry) , electrophile , yield (engineering) , stereochemistry , catalysis , medicinal chemistry , enantioselective synthesis , organic chemistry , materials science , metallurgy
Polycyclic indoline‐benzodiazepines can be accessed through the intermolecular reaction of Tröger bases with N ‐sulfonyl‐1,2,3‐triazoles. Under Rh II 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.