Tetrahedron

Trienediolates of hexadienoic acids in synthesis. Addition to unsaturated ketones. A convergent approach to the synthesis of retinoic acids

MJ Aurell, L Ceita, R Mestres, M Parra, A Tortajada

文献索引：Aurell, Maria J.; Ceita, Luisa; Mestres, Ramon; Parra, Margarita; Tortajada, Amparo Tetrahedron, 1995 , vol. 51, # 13 p. 3915 - 3928

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被引用次数: 14

摘要

The regioselectivity of the addition of the lithium trienediolates generated from hexa-2, 4dienoic acids 1 and 2 or the dihydropyran-2ones 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 retmoic ...