75509-55-6Relevant academic research and scientific papers
A convenient route to 1,4-monoprotected dialdehydes, 1,4-ketoaldehydes, γ-lactols and γ-lactones through radical alkylation of α,β-unsaturated aldehydes in organic and organic-aqueous media
Dondi, Daniele,Caprioli, Ilaria,Fagnoni, Maurizio,Mella, Mariella,Albini, Angelo
, p. 947 - 957 (2007/10/03)
α,β-Unsaturated aldehydes were smoothly alkylated by radicals generated through photosensitised hydrogen abstraction of benzophenone. In this way, and by using 1,3-dioxolane as radical precursor, monoprotected 1,4-dialdehydes were obtained from crotonaldehyde, 2-hexenal, 4-methyl-2-pentenal and cyclohexencarboxyaldehyde in a moderate yield, and in a low yield from β-aryl-α,β-unsaturated aldehydes. With 2-alkyl-1,3-dioxolanes, monoprotected 1,4-ketoaldehydes were analogously prepared. By using methanol, ethanol and isopropanol as radical precursors γ-lactols were likewise obtained from the above aliphatic aldehydes. These single-step syntheses compared favorably with multi-step approaches previously proposed for some of these compounds. The lactols were conveniently oxidized to the corresponding γ-lactones. An alternative to the photosensitisation in organic medium was the use of mixed aqueous-organic solvent and a hydrosoluble photosensitiser (benzophenone disodium disulfonate was prepared for this purpose and successfully used), which allowed a more convenient work up.
Applications of Substituted Arylacetaldehydes in the Total Synthesis of seco-Mesembrane Alkaloids. Part 1. The Total Synthesis of (+/-)-O-Methyljoubertiamine
Forbes, Craig P.,Schoeman, Wentzel J.,Strauss, Heinrich F.,Venter, Elize M. M.,Wenteler, George L.,Wiechers, Adriaan
, p. 906 - 910 (2007/10/02)
The substituted arylacetaldehyde 2-(p-methoxyphenyl)-5-dimethylaminobutanol (1a) is shown to serve as a precursor in the total synthesis of the seco-mesembrane alkaloid (+/-)-O-methyljoubertiamine (2; R1R2=O, R3=Me, Δ
