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Synfacts 2014; 10(5): 0527
DOI: 10.1055/s-0033-1341215
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Reduction of Amides to Alcohols Using SmI2

Contributor(s):
Paul Knochel
,
Diana Haas
Szostak M, * Spain M, Eberhart AJ, Procter DJ. * University of Manchester, UK
Highly Chemoselective Reduction of Amides (Primary, Secondary, Tertiary) to Alcohols Using SmI2/Amine/H2O under Mild Conditions.

J. Am. Chem. Soc. 2014;
136: 2268-2271
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Further Information

Publication History

Publication Date:
17 April 2014 (online)

 
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Key words

reduction - amides - samarium

Significance

The authors report a general procedure for the reduction of primary, secondary and tertiary amides using a SmI2/amine/H2O system. The reaction proceeds under mild conditions and with high selectivity for C–N bond cleavage.


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Comment

In addition, the reduction of enantioenriched amides derived from Myers and Evans auxiliaries was achieved in good yields and high enantioselectivities. These results show that amides with α-enolizable chiral centers can be reduced using this methodology.


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