Abstract
AbstractWe have developed an efficient modular asymmetric synthesis of azahelicenes through an organocatalyzed asymmetric multicomponent reaction from readily available polycyclic aromatic amines, aldehydes, and (di)enamides, by employing a central‐to‐helical chirality conversion strategy. A series of aza[5]‐ and aza[4]helicenes bearing various substituents were readily afforded through this one‐pot sequential enantioselective Povarov reaction/oxidative aromatization process, with good yields and high enantioselectivities. The fruitful and diverse derivatizations of the chiral azahelicene products demonstrated the potential of this method, and a preliminary application of the azahelicene derivative as a chiral organocatalyst was showcased. The photophysical and chiroptical properties of these azahelicenes, particularly the acid/base‐triggered switching of these properties, were also well studied, which may find potential applications in the development of novel organic optoelectronic materials.
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