Brønsted acid-catalyzed efficient Strecker reaction of ketones, amines and trimethylsilyl cyanide.
نویسندگان
چکیده
A general method for the one-pot, three-component Strecker reaction of ketones was developed using Brønsted acids as organocatalysts. A series of alpha-aminonitriles were obtained in good to excellent yields (79-99%). A preliminary extension to a catalytic enantioselective three-component Strecker reaction of ketones (up to 40% ee) is also described.
منابع مشابه
Brønsted acidic ionic liquid as a metal free catalyst for the one-pot synthesis of α-aminonitriles under mild and solvent-free conditions
An efficient, mild and environmentally friendly method was developed for the Strecker reaction to synthesize α-aminonitriles in the presence of methyl imidazolium hydrogen sulfate ([Hmim][HSO4]) as an efficient catalyst. These syntheses were performed via a one-pot three-component condensation of aldehydes (or ketones), amines, and trimethylsilyl cyanide under mild and solvent free c...
متن کاملBrønsted acidic ionic liquid as a metal free catalyst for the one-pot synthesis of α-aminonitriles under mild and solvent-free conditions
An efficient, mild and environmentally friendly method was developed for the Strecker reaction to synthesize α-aminonitriles in the presence of methyl imidazolium hydrogen sulfate ([Hmim][HSO4]) as an efficient catalyst. These syntheses were performed via a one-pot three-component condensation of aldehydes (or ketones), amines, and trimethylsilyl cyanide under mild and solvent free c...
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A simple and efficient one-pot, three-component Strecker reaction of protected amino acids, aromatic aldehydes, and trimethylsilyl cyanide has been developed for the synthesis of chiral α-amino nitriles. The reaction was carried out in the presence of catalytic amount of phosphotungstic acid (H3[P(W3O10)4]) as an environmentally friendly cata...
متن کاملo-Benzenedisulfonimide and its chiral derivative as Brønsted acids catalysts for one-pot three-component Strecker reaction. Synthetic and mechanistic aspects.
o-Benzenedisulfonimide (OBS) has efficiently catalysed the one-pot three-component reaction of ketones and aromatic amines with trimethylsilyl cyanide (TMSCN) giving the corresponding α-amino nitriles in excellent yields (23 examples; average yield 85%). Reaction conditions were very simple, green and efficient. Theoretical calculations have allowed us to explain the mechanism of this reaction ...
متن کاملGallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs.
The synthesis of alpha-aminonitriles and their fluorinated analogs has been carried out in high yield and purity by the Strecker reaction from the corresponding ketones and amines with trimethylsilyl cyanide using gallium triflate in dichloromethane. Monofluoro-, difluro-, or trifluoromethyl groups can be incorporated into the alpha-aminonitrile product by varying the nature of the fluorinated ...
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 8 6 شماره
صفحات -
تاریخ انتشار 2010