Reaction of α-halogeno ketones with carbonyl compounds promoted by CeI3, CeCl3–NaI, or CeCl3–SnCl2
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1473-1477
- https://doi.org/10.1039/p19870001473
Abstract
Reaction of α-halogeno ketones with aldehydes in the presence of CeI3 in tetrahydrofuran is found to give α,β-unsaturated ketones in excellent yields under mild conditions. In contrast, treatment of α-halogeno ketones and carbonyl compounds with CeCl3–NaI or CeCl3–SnCl2 affords β-hydroxy ketones in good yields. It is assumed that these reactions proceed via cerium enolates. The combined reagents, however, cannot be applied to a Reformatsky-type reaction. Regiospecific and aldehyde chemoselective aldol synthesis are also described.Keywords
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