ON THE DIRECT METALATION OF ISOPRENE

被引：39

作者：

KLUSENER, PAA ^{[1
]}

TIP, L ^{[1
]}

BRANDSMA, L ^{[1
]}

机构：

[1] UNIV UTRECHT,DEBYE INST,DEPT PREPARAT ORGAN CHEM,PADUALAAN 8,3584 CH UTRECHT,NETHERLANDS

来源：

TETRAHEDRON | 1991年 / 47卷 / 10-11期

关键词：

D O I：

10.1016/S0040-4020(01)96114-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isoprene has been metalated in tetrahydrofuran with an excess of sterically hindered potassium dialkylamides, prepared by combining equimolar amounts of the corresponding lithium amide and potassium tert-butoxide. Subsequent reaction with oxirane, alkyl bromides, and pivaldehyde gave the expected coupling products in reasonable yields. Coupling with (CH3)2CHCH2CH = O and (CH3)2C = CHCH = O afforded the bark beetle pheromones (+/-)-ipsenol and (+/-)-ipsdienol in low yields.

引用

页码：2041 / 2064

页数：24

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