[Development of acid-base organocatalysts for enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reactions via dual activation mechanism].
This review describes our recent efforts in the development of acid-base organocatalysts, (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl) BINOL (6a) and (S)-3-[2-(diphenylphosphino)phenyl] BINOL (13a), with dual activation mechanism for the aza-Morita-Baylis-Hillman (aza-MBH) reaction. In these catalysts, chiral Brønsted acid units are connected with a Lewis base unit via a spacer. The acid-base moieties act cooperatively as an enzyme-mimetic catalyst to activate substrates in the carbon-carbon bond forming reaction between enones and N-tosylimines with high enantioselectivity.
The Institute of Scientific and Industrial Research, Osaka University, Ibaraki, Osaka, Japan. taki@sanken.osaka-u.ac.jp
Shinobu
S
Takizawa
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D007093:Imidazoles; D009284:Naphthols; D055601:Organic Chemistry Phenomena; D010720:Phosphines; D011725:Pyridines; D013237:Stereoisomerism
C406944:BINOL, naphthol; D007093:Imidazoles; D009284:Naphthols; D010720:Phosphines; D011725:Pyridines