A facile method for the synthesis of oxindole based quaternary alpha-aminonitriles via the Strecker reaction.
The direct alpha-cyanoamination of isatins using TMSCN has been developed, which is carried out in methanol without any catalyst. A new bifunctional cinchona alkaloid-based phosphinamide catalyst 7 could promote the Strecker reaction of isatins derived ketimine with TMSCN in up to 74% ee.
Liu
Yun-Lin
YL
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, P. R. China.
Zhou
Feng
F
Cao
Jun-Jie
JJ
Ji
Cong-Bin
CB
Ding
Miao
M
Zhou
Jian
J
D000588:Amines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D000078183:Oxindoles; D013237:Stereoisomerism
D000588:Amines; D007211:Indoles; D009570:Nitriles; D000078183:Oxindoles; C022960:2-oxindole