Highly practical catalytic asymmetric 1,4-addition of arylboronic acids in water using new hydrophilic chiral bicyclo[3.3.0] diene ligands.
The first Rh-diene-catalyzed aqueous asymmetric 1,4-addition of alpha,beta-unsaturated carbonyl compounds with arylboronic acids has been realized. By using a hydrophilic bicyclo[3.3.0] diene ligand, the reactions can be performed successfully in neat water at room temperature to afford the corresponding products in good yields and with very high enantioselectivities for both cyclic and linear substrates.
Feng
Chen-Guo
CG
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Wang
Zhi-Qian
ZQ
Shao
Cheng
C
Xu
Ming-Hua
MH
Lin
Guo-Qiang
GQ
D000475:Alkenes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D000475:Alkenes; D001897:Boronic Acids; D001643:Bridged Bicyclo Compounds; D008024:Ligands; D014867:Water