Brønsted acid-catalyzed efficient Strecker reaction of ketones, amines and trimethylsilyl cyanide

Brønsted acid-catalyzed efficient Strecker reaction of ketones, amines and trimethylsilyl cyanide

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 r...

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Veröffentlicht in:Organic & biomolecular chemistry 2010-03, Vol.8 (6), p.1399-1405
Hauptverfasser: Zhang, Guang-Wu, Zheng, Dong-Hua, Nie, Jing, Wang, Teng, Ma, Jun-An
Format: Artikel
Sprache:eng
Schlagworte:
Acids - chemistry
Amines - chemistry
Catalysis
Cyanides - chemistry
Ketones - chemistry
Magnetic Resonance Spectroscopy
Spectrometry, Mass, Electrospray Ionization
Trimethylsilyl Compounds - chemistry
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b924272d