Details

Autor(en) / Beteiligte

• Fang, Zhi-Jia
• Zheng, Sheng-Cai
• Guo, Zhen
• Guo, Jing-Yao
• Tan, Bin
• Liu, Xin-Yuan

Titel

Asymmetric Synthesis of Axially Chiral Isoquinolones: Nickel-Catalyzed Denitrogenative Transannulation

Ist Teil von

• Angewandte Chemie (International ed.), 2015-08, Vol.54 (33), p.9528-9532

Auflage

International ed. in English

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2015

Quelle

MEDLINE

Beschreibungen/Notizen

• The first Ni0/bis(oxazoline)‐catalyzed asymmetric denitrogenative transannulation of 1,2,3‐benzotriazin‐4(3H)‐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. Getting the axe: Reported is the first enantioselective Ni0/bis(oxazoline)‐catalyzed asymmetric transannulation of 1,2,3‐benzotriazin‐4(3H)‐ones with internal alkynes in an atroposelective manner to form novel axially chiral isoquinolones. DFT calculations show data for the preferred transition state in the annulation step. The products show good cytotoxicity against cancer cell lines.