Tetrahedron

Preparation of 2-alkyl-and 2-acylpropenals from 5-(trifluoromethanesulfonyloxy)-4H-1, 3-dioxin: a versatile acrolein α-cation synthon

SP Fearnley, RL Funk, RJ Gregg

文献索引：Fearnley, Stephen P.; Funk, Raymond L.; Gregg, Robert J. Tetrahedron, 2000 , vol. 56, # 52 p. 10275 - 10281

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被引用次数: 13

摘要

5-(Trifluoromethanesulfonyloxy)-4H-1, 3-dioxin (3) participates in a variety of nucleophilic substitution reactions with cuprate reagents or in palladium catalyzed cross-coupling reactions to provide 5-substituted-4H-1, 3-dioxins 5. Upon thermolysis, these compounds undergo facile retrocycloaddition reactions to generate the corresponding 2-substituted acroleins which, if necessary, can be trapped in situ with dienes or heterodienophiles. In ...