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Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands
Author(s) -
Redero Pablo,
Hartung Thierry,
Zhang Jianwei,
Nicholls Leo D. M.,
Zichen Guo,
Simon Martin,
Golz Christopher,
Alcarazo Manuel
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202010021
Subject(s) - enantioselective synthesis , cationic polymerization , chemistry , aryl , combinatorial chemistry , yield (engineering) , catalysis , reactivity (psychology) , organic chemistry , materials science , alkyl , medicine , alternative medicine , pathology , metallurgy
Abstract The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in Au I 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 Au I ‐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.