Chiral boryl radical catalyzed asymmetric radical cycloisomerization

• Main Authors: Jin, Jiamiao, Ren, Shi-Chao, Chi, Robin Yonggui
• Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
• Format: Article
• Language: English
• Published: 2024
• Subjects: Chemistry; Multidisciplinary
• Online Access: https://hdl.handle.net/10356/179293
• Institution: Nanyang Technological University

Asymmetric catalytic organic synthesis is of profound importance in modern research and industries, providing optically enriched molecules with diverse structures and functions [1]. Enzymes, transition metal complexes, and simple organic molecules have all been found as powerful catalysts that enable the bond breaking and forming events with excellent control over stereo-selectivity matters. In the realm of designed small molecule organic catalysts, the majority of (active) catalytic species are based on the transfer of electron pairs (such as amines and N-heterocyclic carbenes (NHC) behaving as nucleophilic catalysts) or empty orbitals (such as Brønsted or Lewis acid catalysts) to enable the substrate activation and initiate the catalytic process. Although certain catalytic reaction steps involving these organic catalysts can be designed to go through radical processes, the catalysts themselves behaving as radical species to initiate asymmetric reactions are rarely explored. As of present, radical catalyst-mediated reactions in this regard (such as those catalyzed by thiol radicals, stannyl radicals, nitrogen radicals, and bromine radicals) mostly do not involve chiral controls. Limited success in using radical catalysts for asymmetric reactions includes Zhang’s cobalt-based metalloradical and Maruoka and Miller’s thiol radical catalysts