Enantioselective Synthesis of 1‐Aryl Benzohelicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands

The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in AuI catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular syn...

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Bibliographic Details
Published in:Angewandte Chemie 2020-12, Vol.132 (52), p.23733-23737
Main Authors: Redero, Pablo, Hartung, Thierry, Zhang, Jianwei, Nicholls, Leo D M, Guo Zichen, Martin, Simon, Golz, Christopher, Alcarazo, Manuel
Format: Article
Language:English
Subjects:
Alkynes
Aromatic compounds
Catalysis
Cations
Chemistry
Enantiomers
Ligands
Optimization
Synthesis
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Summary:The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in AuI catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular synthesis of these ligands and the enhanced reactivity that they impart to AuI‐centers after coordination have been found to be the key features that allow an optimization of the reaction conditions until the desired benzo[5]helicenes are obtained with high yield and enantioselectivity.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202010021