Supramolecular Architecture of an Amphiphilic Amino Alcohol as a Versatile Chiral Environment for Stereocontrolled Photoreaction of Various Anthracenes

• Published in: Chemistry : a European journal Vol. 28; no. 62; pp. e202201940 - n/a
• Main Authors: Kanai, Hayato, Yamada, Kuniyo, Salikolimi, Krishnachary, Kodama, Koichi, Ishida, Yasuhiro
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 07.11.2022
• Subjects: Amides; anthracenes; asymmetric photochemistry; Chemistry; Esters; liquid crystals; Photochemistry; pre-organization; supramolecular polymers
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202201940

The photocyclodimerization of 2‐anthracenecarboxylic acid has been extensively studied as a model reaction of asymmetric photochemistry. So far, numerous chiral environments have been employed to control this photoreaction, while the scope of photoreactants has been limited only to 2‐anthracenecarboxylic acid and its simple esters and amides. Here, we developed a systematic series of photoreactants (2 a–d) by introducing various substituents to 2‐anthracenecarboxylic acid, which showed different reactivities and selectivities depending on the substituents. By using the photoreactants 2 a–d, we evaluated the performance of a chiral environment composed of an amphiphilic amino alcohol (1), where the photocyclodimerization of 2 a–d generally proceeded in excellent regio‐ and enantioselectivities (71–98 % regio ratio, 76–86 % ee). Furthermore, by reacting 2 a and 2 b together in the chiral environment of 1, we succeeded in the first stereocontrolled cross‐photocyclodimerization between two prochiral anthracenes (58 % chemo ratio, 83 % regio ratio, 90 % ee). Supramolecular architecture of an amphiphilic amino alcohol serves as unprecedentedly versatile chiral environment, which can efficiently control the stereochemistry of the self‐photocyclodimerization of various anthracenes (71–98 % regio ratio, 76–86 % ee) as well as the cross‐photocyclodimerization between two anthracenes (58 % chemo ratio, 83 % regio ratio, 90 % ee).