Tetrahedron

Efficient preparation of 3-substituted-furan-2 (5H)-ones and their direct vinylogous aldol addition

M Bella, G Piancatelli, A Squarcia

文献索引：Bella, Marco; Piancatelli, Giovanni; Squarcia, Antonella Tetrahedron, 2001 , vol. 57, # 20 p. 4429 - 4436

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被引用次数: 25

摘要

The deprotonation of 3-substituted-furan-2 (5H)-ones 1, obtained via the hydrolysis of 3- substituted-2, 5-dihydro-2, 5-dimethoxyfurans, affords in the reaction with both aromatic and aliphatic aldehydes regioselectively the unsaturated 3-substituted 5-(1′-hydroxy)-γ- butyrolactones, such as 4, 5, 6, 7, 8, 9 and 10. The use of Lewis acids allows modulation of the diastereoisomeric ratios. The subsequent reduction, carried out with nickel boride, ...