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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Doi:10.1021/ol401483j
(2013)Doi:10.1021/jo00052a001
(1992)Doi:10.1039/c3ob40445e
(2013)Doi:10.1039/c3ob40614h
(2013)Doi:10.1016/j.tet.2013.05.083
(2013)Doi:10.1002/chem.202003445
(2021)
