Enantioselective Synthesis of 1,12‐Disubstituted (4) Helicenes

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Abstract: 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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Enantioselective Synthesis of 1,12‐Disubstituted (4) Helicenes ; volume:59 ; number:14 ; year:2020 ; pages:5660-5664 ; extent:5
Angewandte Chemie / International edition. International edition ; 59, Heft 14 (2020), 5660-5664 (gesamt 5)

Creator: Hartung, Thierry
Machleid, Rafael
Simon, Martin
Golz, Christopher
Alcarazo, Manuel

DOI: 10.1002/anie.201915870

URN: urn:nbn:de:101:1-2022061113025800823497

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:31 AM CEST

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Associated

Hartung, Thierry
Machleid, Rafael
Simon, Martin
Golz, Christopher
Alcarazo, Manuel

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