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Enantioselective Synthesis of 1,12‐Disubstituted [4]Helicenes
Author(s) -
Hartung Thierry,
Machleid Rafael,
Simon Martin,
Golz Christopher,
Alcarazo Manuel
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201915870
Subject(s) - enantioselective synthesis , cationic polymerization , intramolecular force , chemistry , alkyne , substrate (aquarium) , combinatorial chemistry , dioxolane , catalysis , stereochemistry , organic chemistry , oceanography , geology
A highly enantioselective synthesis of 1,12‐disubstituted [4]carbohelicenes is reported. The key step for the developed synthetic route is a Au‐catalyzed intramolecular alkyne hydroarylation, which is achieved with good to excellent regio‐ and enantioselectivity by employing TADDOL‐derived (TADDOL=α,α,α,α‐tetraaryl‐1,3‐dioxolane‐4,5‐dimethanol) α‐cationic phosphonites as ancillary ligands. Moreover, an appropriate design of the substrate makes the assembly of [4]helicenes of different substitution patterns possible, thus demonstrating the synthetic utility of the method. The absolute stereochemistry of the newly prepared structures was determined by X‐ray crystallography and characterization of their photophysical properties is also reported.