Access to Chiral Rigid Hemicyanine Fluorophores from Tröger Bases and α-Imino Carbenes | Zendy

Nidal Saleh | Zendy; Alessandro Bosmani | Zendy; Céline Besnard | Zendy; Thomas Bürgi | Zendy; Denis Jacquemin | Zendy; Jérôme Lacour | Zendy

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Access to Chiral Rigid Hemicyanine Fluorophores from Tröger Bases and α-Imino Carbenes

Author(s) -

Nidal Saleh,

Alessandro Bosmani,

Céline Besnard,

Thomas Bürgi,

Denis Jacquemin,

Jérôme Lacour

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02726

Subject(s) - chemistry , combinatorial chemistry , catalysis , stereochemistry , organic chemistry

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 oxidation. 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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