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In Luche’s 1978 article in the Journal of Organic Chemistry, Luche, et. al. combined cerium trichloride, as well as other members of the lanthanide series, with sodium borohydride and various unsaturated ketones in order to form allylic alcohols. The selectivity and yields of allylic alcohols in reactions with cerium trichloride were compared to those from the starting ketones reacting with other lanthanides. The ketone reactions with cerium and samarium produced the most selective allylic alcohol products in the highest yield. 1, 2 reduction of the ketones occurred consistently, even with the presence of functional groups such as carboxylic acids, esters, amides, halides, and cyano and nitro groups, which remained untouched. Luche, et. al. hypothesized possible reaction mechanisms in the lanthanide reduction: a reduction by a lanthanide borohydride (which would account for the regioselectivity) or a reduction by sodium borohydride of a lanthanide-carbonyl complex. It was concluded that a reaction involving a lanthanide as a catalyst is unlikely, as is a reduction by the lanthanide alone, since lanthanides are not very reactive with ketones.
J. L. J. Am. Chem. Soc. 1978, 100, 2226-2227.
Hayashi, N.; Suzuki, T.; Usui, K.; Nakada, M. Tetrahedron. 2009, 65, 888-895.
The Luche reduction of a ketone was used as a step in the synthesis of (+)-phomopsidin, a microtubule protein; the Luche reaction was chosen as the method of reduction due to it
is high selectivity and high yield.
Cavezza, A.; Boulle, C.; Gueguiniat, A.; Pichaud, P.; Trouille, S.; Ricard, L.; Dalko-Csiba, M. Bioorgan. Med. Chem. 2009, 19, 845-849.
NaBH4/CeCl3 (Luche reduction reagent) was one of many reducing agents used in this article to see the effects of solvent, acid, and reducing agent on the reduction of C-xyloside.
Gollner, A.; Mulzer, J. Org. Lett. 2008, 10, 4701-4704.
In the process of synthesizing neolaulimalide, Gollner and Mulzer used Luche reducing reagents at low temperatures to yield product with good diatereoselectivity.