Reaction of alpha,beta-unsaturated and alpha-phenyl acetals with epoxides, promoted by lithium-potassium mixed base LICKOR: Synthesis of homoallyl alcohols

被引：21

作者：

Deagostino, A ^{[1
]}

Prandi, C ^{[1
]}

Venturello, P ^{[1
]}

机构：

[1] UNIV TURIN,IST CHIM ORGAN,I-10125 TURIN,ITALY

来源：

TETRAHEDRON | 1996年 / 52卷 / 04期

关键词：

D O I：

10.1016/0040-4020(95)00969-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetals 1, 7 and 8, in the presence of the mixed metal base LICKOR undergo deprotonation and elimination reactions, affording enol ethers intermediates. Further hydrogen-metal exchange at the alpha-vinyl site of elimination products gives alpha-metalated species that yield, by reaction with epoxides, homoallyl alcohols. Experimental procedures are given for the conversion of the unsaturated species into the corresponding carbonyl compounds. alpha-Substituted ethoxy diene 4 is also an useful intermediate for a one-pot synthesis of 2,6-disubstituted tetrahydro-4H-pyran-4-one 19.

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页码：1433 / 1442

页数：10

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