Iridium-catalyzed regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane.
Highly regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane (FBSM) has been realized by [Ir(COD)Cl](2)/phosphoramidite, affording enantiopure fluorobis(phenylsulfonyl)methylated compounds bearing a terminal alkene, which could be converted to monofluoro-methylated ibuprofen in just two steps without loss of the optical purity (95% ee).
Liu
Wen-Bo
WB
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.
Zheng
Sheng-Cai
SC
He
Hu
H
Zhao
Xiao-Ming
XM
Dai
Li-Xin
LX
You
Shu-Li
SL
D000478:Alkylation; D002384:Catalysis; D018360:Crystallography, X-Ray; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism
D006845:Hydrocarbons, Fluorinated; C546375:fluorobis(phenylsulfonyl)methane; D007495:Iridium; D008697:Methane