Asymmetric Synthesis of Spiropyrazolones by Rhodium-Catalyzed C(sp2)-H Functionalization/Annulation Reactions.
Rhodium-catalyzed C(sp2)-H functionalization reactions of 4-aryl-5-pyrazolones followed by [3+2] annulation reactions with alkynes provide rapid access to highly enantioenriched five-membered-ring 4-spiro-5-pyrazolones. The use of a chiral SCpRh catalyst enabled the synthesis of a large range of spiropyrazolones with all-carbon quaternary stereogenic centers in up to 99 % yield and 98 % ee from readily available substrates.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Jun
J
Zheng
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Shao-Bo
SB
Wang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Chao
C
Zheng
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.|Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072, China.
Shu-Li
0000-0003-4586-8359
SL
You
C-H functionalization; alkynes; asymmetric catalysis; pyrazolones; rhodium