Catalytic asymmetric deuterosilylation of exocyclic olefins with mannose-derived thiols and deuterium oxide. Issue 5 (23rd January 2023)

• Record Type: Journal Article
• Authors: Ramanathan, Devenderan; Shi, Qinglong; Xu, Meichen; Chang, Rui; Peñín, Beatriz; Funes-Ardoiz, Ignacio; Ye, Juntao
• Is Part Of: Organic chemistry frontiers. Volume 10:Issue 5(2023)
• Page Start: 1182
• Page End: 1190
• Publication Date: 2023-01-23
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01979e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Metal-free, photoinduced asymmetric deuterosilylation of exocyclic olefins has been achieved using a mannose-derived thiol catalyst. Abstract : Here we report a photochemical approach for asymmetric deuterosilylation of exocyclic olefins by utilizing mannose-derived thiols as the chiral catalyst and inexpensive deuterium oxide as the deuterium source. DFT computational studies reveal that multiple non-covalent interactions between the thiol catalyst and the radical adduct are responsible for controlling the enantioselectivity of the reaction.