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- Title
Enantioselective CH Bond Functionalization Triggered by Radical Trifluoromethylation of Unactivated Alkene.
- Authors
Yu, Peng; Lin, Jin ‐ Shun; Li, Lei; Zheng, Sheng ‐ Cai; Xiong, Ya ‐ Ping; Zhao, Li ‐ Jiao; Tan, Bin; Liu, Xin ‐ Yuan
- Abstract
An asymmetric unactivated alkene/CH bond difunctionalization reaction for the concomitant construction of CCF3 and CO bonds was realized by using a Cu/Brønsted acid cooperative catalytic system, thus providing facile access to valuable chiral CF3-containing N,O-aminals with excellent regio-, chemo-, and enantioselectivity. Mechanistic studies revealed that this reaction may proceed by an unprecedented 1,5-hydride shift involving activation of unactivated alkenes and a radical trifluoromethylation to initiate subsequent enantioselective functionalization of CH bonds. Control experiments also suggested that chiral Brønsted acid plays multiple roles and not only controls the stereoselectivity but also increases the reaction rate through activation of Togni's reagent.
- Subjects
ALKENES; HYDROGEN bonding; CHEMICAL reactions; ENANTIOSELECTIVE catalysis; CHEMICAL research
- Publication
Angewandte Chemie, 2014, Vol 126, Issue 44, p12084
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201405401