- Access to Chiral Rigid Hemicyanine Fluorophores from Tröger Bases and α-Imino Carbenes
Nidal Saleh, Alessandro Bosmani, Céline Besnard, Thomas Bürgi, Denis Jacquemin, Jérôme Lacour
Org. Lett. 2020, 22, 7599-7603
Chiral hemicyanine fluorophores are afforded in three steps only from Tröger bases via α-imino carbene additions, an original aminal deprotection and Cu(II)-mediated oxidations. The stable benzodiazepinoindolium salts are readily isolated and present (chir)optical properties that can be fine-tuned by late-stage cross-coupling functionalization. The hemicyanine character of dyes was rationalized using first principles.
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