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

Polycyclic Indoline-Benzodiazepines by Electrophilic Additions of α-Imino Carbenes to Tröger Bases.
Angew Chem Int Ed Engl. 2018 Apr 19;:
Authors: Bosmani A, Guarnieri-Ibáñez A, Goudedranche S, Besnard C, Lacour J
Abstract
Polycyclic indoline-benzodiazepines are afforded by 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 incl. two bridgehead N-atoms). Further ring-expansion by insertion of a second α-imino carbene leads to elaborated polycyclic 9-membered ring triazonanes.
PMID: 29673027 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - April 19, 2018 Category: Chemistry Authors: Bosmani A, Guarnieri-Ibáñez A, Goudedranche S, Besnard C, Lacour J Tags: Angew Chem Int Ed Engl Source Type: research