Catalytic Asymmetric Mannich-Type Reaction of an α-Trifluoromethyl Amide

Direct Catalytic Asymmetric Mannich-Type Reaction of an α-CF3 Amide to Isatin Imines: J.-S. Yu, H. Noda, N. Kumagai, M. Shibasaki
Synlett 2019, DOI: 10.1055/s-0037-1611642


Trifluoromethyl-substituted amines have found important applications in medicinal chemistry and materials science. Being non-natural xenobiotic compounds, the only source of CF3-amines is synthesis, which explains the enormous interest these compounds have generated in the organic chemistry community. Recently, the group of Professor Masakatsu Shibasaki from the Institute of Microbial Chemistry (Tokyo, Japan), reported a direct and stereocontrolled entry to β-CF3 amines – incorporating a 2-indolinone unit – using extremely direct and simple Mannich-type chemistry, relying on an α-CF3 amide and isatin imines as substrates.

Professor Shibasaki said: “The merger of our longstanding interests in direct enolization with fluorine chemistry has opened up the new way to produce important chiral building blocks.”
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