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|Title:||Kinetic and dynamic kinetic resolution of racemic tertiary bromides by pentanidium‐catalyzed phase‐transfer azidation||Authors:||Ren, Jingyun
Tan, Siu Min
|Keywords:||Science::Chemistry||Issue Date:||2020||Source:||Ren, J., Ban, X., Zhang, X., Tan, S. M., Lee, R. & Tan, C. (2020). Kinetic and dynamic kinetic resolution of racemic tertiary bromides by pentanidium‐catalyzed phase‐transfer azidation. Angewandte Chemie, 132(23), 9140-9143. https://dx.doi.org/10.1002/ange.202000138||Project:||2019-T1-001-107
|Journal:||Angewandte Chemie||Abstract:||We have developed a method to afford enantiomerically enriched tertiary azides and bromides through pentanidium-catalyzed kinetic resolution (KR) of racemic tertiary bromides under base-free conditions. We found that the absence of water is crucial to attain a high selectivity factor (s). On the other hand, new experimental observations and DFT modeling led us to propose that enantioconvergent azidation of tertiary bromides proceeded through dynamic kinetic resolution (DKR). The investigations particularly identified the crucial roles of base and water in the enantioconvergent process, thus supporting the proposal that the tertiary bromide isomerizes in the presence of base and water through a SN2X pathway.||URI:||https://hdl.handle.net/10356/170451||ISSN:||0044-8249||DOI:||10.1002/ange.202000138||Schools:||School of Chemistry, Chemical Engineering and Biotechnology||Rights:||© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. All rights reserved.||Fulltext Permission:||none||Fulltext Availability:||No Fulltext|
|Appears in Collections:||CCEB Journal Articles|
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