6636-32-4Relevant articles and documents
Ustynyuk et al.
, p. C53 (1971)
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Kissmann et al.
, p. 3949 (1952)
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Preparation of Indolenines via Nucleophilic Aromatic Substitution
Huber, Florian,Roesslein, Joel,Gademann, Karl
, p. 2560 - 2564 (2019/03/19)
An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples were further converted to the corresponding indolenine dyes. Key experiments provide insight into the mechanism of this nucleophilic aromatic substitution.
Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation
Lackner, Aaron D.,Samant, Andrew V.,Toste, F. Dean
supporting information, p. 14090 - 14093 (2013/10/21)
The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asymmetric redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture. The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.
