Enantioselective Morita-Baylis-Hillman reaction of isatins with acrylates: facile creation of 3-hydroxy-2-oxindoles.
The first tertiary amine catalyzed enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins with acrylates has been demonstrated, allowing asymmetric synthesis of biologically significant 3-substituted-3-hydroxy-2-oxindoles in good yields and with excellent enantioselectivities. The C6'-OH group of β-isocupreidine (β-ICD) is believed to facilitate the key proton transfer step in the MBH reaction, via an intramolecular proton relay process.
Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Republic of Singapore, 117543.
Fangrui
F
Zhong
Guo-Ying
GY
Chen
Yixin
Y
Lu
D000179:Acrylates / Q000737:chemistry*; D002384:Catalysis; D006900:Hydroxylation; D007211:Indoles / Q000138:chemical synthesis*; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013237:Stereoisomerism
D000179:Acrylates; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D007510:Isatin; C036658:acrylic acid