Tetrahedron Letters p. 5051 - 5054 (1992)
Update date:2022-07-29
Topics:
Duhamel, Lucette
Guillemont, Jerme
Poirier, Jean-Marie
Bromination of enamines of prenal and crotonaldehyde yields the corresponding ω-bromoaldehydes via the simple hydrolysis of iminium salts. The carbonyl function of these aldehydes can be protected as acetals or dioxolane. The overall process can be realized in a one pot procedure. The dioxolane is the starting material of a phosphonate which allows,by condensation with β-ionylidenacetaldehyde a direct access to the retinal with a 27.5% overall yield from the enamine 2.
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