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- Title
Kinetic and Dynamic Kinetic Resolution of Racemic Tertiary Bromides by Pentanidium‐Catalyzed Phase‐Transfer Azidation.
- Authors
Ren, Jingyun; Ban, Xu; Zhang, Xin; Tan, Siu Min; Lee, Richmond; Tan, Choon‐Hong
- 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.
- Subjects
KINETIC resolution; AZIDATION; BROMIDES; AZIDES
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 23, p9140
- ISSN
0044-8249
- Publication type
Academic Journal
- DOI
10.1002/ange.202000138