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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.


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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.


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Review

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


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