131189-97-4Relevant academic research and scientific papers
Trienediolates of hexadienoic acids in synthesis. Addition to unsaturated ketones. A convergent approach to the synthesis of retinoic acids
Aurell, Maria J.,Ceita, Luisa,Mestres, Ramon,Parra, Margarita,Tortajada, Amparo
, p. 3915 - 3928 (1995)
The regioselectivity of the addition of the lithium trienediolates generated from hexa-2,4-dienoic acids 1 and 2 or the dihydropyran-2-ones 4 and 5 to unsaturated ketones 6 is studied. Equilibration conditions favour reaction of the trienediolates through their ω carbon, and the ketones according to 1,2- and 1,4-additions. β-Ionone 6a and the aryl-butenone 6b lead to the 1,2-ω-adducts 8, which undergo a facile acid catalyzed dehydration to retinoic acids 11. On reaction with the unsaturated ketone 6b or with the aryl ketones 21, the trimethyldihydropyran-2-one 5 leads to γ'-adducts derived from deprotonation of the chain methyl substituent along with the 1,4-ω-adducts.
Polyenolates of unsaturated carboxylic acids in synthesis. A straightforward synthesis of retinoic acids
Aurell,Parra,Tortajada,Gil,Mestres
, p. 5791 - 5794 (2007/10/02)
Retinoic acids are prepared in a two step procedure by addition of lithium trienediolates of sorbic acid and 3-methyl-sorbic acid to β-ionone.
