Amide activation by TMSCl: reduction of amides to amines by LiAlH4 under mild conditions

Amide activation by TMSCl: reduction of amides to amines by LiAlH4 under mild conditions

An expeditious and practical method for the reduction of amides to amines is reported. The method consists of activation of amides with TMSCl followed by reduction with LiAlH4. Various amides/lactams including hindered amides and secondary amides gave the corresponding amines in good to excellent yi...

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Veröffentlicht in:Tetrahedron letters 2013-09, Vol.54 (36), p.4908-4913
Hauptverfasser: Ravinder, B., Rajeswar Reddy, S., Panasa Reddy, A., Bandichhor, Rakeshwar
Format: Artikel
Sprache:eng
Schlagworte:
Activation
Amides
Amines
Functional groups
Lithium aluminum hydride
Reduction
Reductive amination
Tetrahedrons
Tolerances
Trimethylsilyl chloride
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Beschreibung
Zusammenfassung:An expeditious and practical method for the reduction of amides to amines is reported. The method consists of activation of amides with TMSCl followed by reduction with LiAlH4. Various amides/lactams including hindered amides and secondary amides gave the corresponding amines in good to excellent yields. This novel protocol has a wide substrate scope and shows good functional group tolerance with high stereoretention.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.06.144