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Synfacts 2019; 15(02): 0153
DOI: 10.1055/s-0037-1611988
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

1,2-Reduction of Conjugated Ketones: The Luche Reduction

Contributor(s):
Paul Knochel
,
Moritz Balkenhohl
Luche J.-L. * Université Scientifique et Médicale, Grenoble, France
Lanthanides in Organic Chemistry. 1. Selective 1,2 Reductions of Conjugated Ketones.

J. Am. Chem. Soc. 1978;
100: 2226-2227
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Further Information

Publication History

Publication Date:
18 January 2019 (online)

 
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Key words

allylic alcohols - Luche reduction - lanthanide salts

Significance

In 1978, Luche reported the selective 1,2-reduction of α,β-unsaturated ketones by using sodium borohydride in the presence of various lanthanide chlorides, leading to allylic alcohols in excellent yields.


 

Comment

Remarkably, the use of lanthanide salts allowed the selective 1,2-reduction of several unsaturated ketones. Additionally, the undesired 1,4-reduction product was not formed which, until then, was a common byproduct in metal hydride mediated reduction methods.


 

Review

G. A. Molander Chem. Rev. 1992, 92, 29–68.


 

 


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