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- Title
Asymmetric Synthesis of Axially Chiral Isoquinolones: Nickel-Catalyzed Denitrogenative Transannulation.
- Authors
Fang, Zhi ‐ Jia; Zheng, Sheng ‐ Cai; Guo, Zhen; Guo, Jing ‐ Yao; Tan, Bin; Liu, Xin ‐ Yuan
- Abstract
The first Ni0/bis(oxazoline)-catalyzed asymmetric denitrogenative transannulation of 1,2,3-benzotriazin-4(3 H)-ones with bulky internal alkynes to form novel axially chiral isoquinolones in an atroposelective manner has been developed. This method provides direct asymmetric access to axially chiral isoquinolones with excellent functional-group tolerance in excellent yields and stereoselectivities from readily available starting materials under mild reaction conditions. These axially chiral isoquinolones exhibit high cytotoxicity against a number of human cancer cell lines. DFT calculations reveal the nature of the transition state in the key annulation step.
- Subjects
ISOQUINOLINE; ASYMMETRIC synthesis; NICKEL catalysts; CHIRALITY; NITROGEN; STEREOSELECTIVE reactions; CELL-mediated cytotoxicity
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 33, p9664
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201503207