Diastereoselective synthesis of N-aryl tetrahydroquinolines and N-aryl indolines by the tandem reaction of arynes.
A tandem reaction of arynes with α- or β-amino ketones has been revealed. Arynes react with β-amino ketones through a cascade insertion-cyclization process to afford N-aryl tetrahydroquinolines in good yield with excellent anti-selectivity. Meanwhile, the coupling of arynes with α-amino ketones produces multisubstituted indolines in high yield with syn-selectivity. A quaternary carbon center can be constructed in this process, and the reaction can be easily scaled up.
School of Chemistry and Chemical Engineering, Shihezi University , Xinjiang, Uygur Autonomous Region 832000, China.
Ji-Xin
JX
Pian
Lin
L
He
Guang-Fen
GF
Du
Hao
H
Guo
Bin
B
Dai
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D007211:Indoles; D007659:Ketones; D011804:Quinolines; C057812:indoline; C542964:1,2,3,4-tetrahydroquinoline