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Issue 3, 1990
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New method for the selective reduction of amides

Shwu-Chen Tsay,  Jeffrey A. Robl  and  Jih Ru Hwu 

Abstract

A new procedure was developed for the reduction of tertiary aliphatic, olefinic, and aromatic amides to aldehydes. Reaction of the amides (1), (5), (7), (9), (11), (13), (15), and (17) with ethyl or methyl trifluoromethanesulphonate in CH2Cl2 at room temperature and then with L-Selectride at –78 °C gave the corresponding aldehydes (2), (6), (8), (10), (12), (14), (16), and (18), respectively. A second functional group, including CO2R, C[double bond, length half m-dash]C, CH(OCH2CH2O), and C[triple bond, length half m-dash]N, in these amides was found to be inert under the conditions employed. These selective reductions gave the desired aldehydes in 50–73% isolated yields and in >95% yields based on converted amides.

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Article type: Paper
DOI: 10.1039/P19900000757
Citation: J. Chem. Soc., Perkin Trans. 1, 1990,0, 757-759
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    New method for the selective reduction of amides

    S. Tsay, J. A. Robl and J. R. Hwu, J. Chem. Soc., Perkin Trans. 1, 1990, 0, 757
    DOI: 10.1039/P19900000757

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