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Controlled and Chemoselective Reduction of Secondary Amides

Guillaume Pelletier, William S. Bechara and André B. Charette*

*Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7, Email: andre.charetteumontreal.ca

G. Pelletier, W. S. Bechara, A. B. Charette, J. Am. Chem. Soc., 2010, 132, 12817-12819.

DOI: 10.1021/ja105194s (free Supporting Information)


Abstract

A chemoselective activation of a secondary amide with triflic anhydride in the presence of 2-fluoropyridine enables a mild reduction using triethylsilane, a cheap and rather inert reagent. Imines can be isolated after a basic workup or readily transformed to the aldehydes following an acidic workup. The amine moiety can be accessed by addition of Hantzsch ester to the reaction mixture.

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Key Words

aldehydes, imines, amines, triethylsilane, Hantzsch ester


ID: J48-Y2010-2610