Functionalization of the methyl ketone fragment in 1-[(1S,3R)-2,2-dimethyl-3-(2-methoxymethyloxyethyl)cyclo- propyl]-2-propanone

被引：2

作者：

Gimalova, FA ^{[1
]}

Sadretdinov, IF ^{[1
]}

Spirikhin, LV ^{[1
]}

Miftakhov, MS ^{[1
]}

机构：

[1] Russian Acad Sci, Ufa Res Ctr, Inst Organ Chem, Ufa 450054, Bashkortostan, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 39卷 / 09期

关键词：

D O I：

10.1023/B:RUJO.0000010207.63528.f6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deprotonation of 1-[(1S,3R)-2,2-dimethyl-3-(2-methoxymethyloxyethyl)cyclopropyl]-2-propanone with lithium diisopropylamide in THF at -78degreesC and subsequent treatment of the resulting enolate with Me3SiCl yielded mainly the corresponding terminal silyl enol ether. The condensation of intermediate enolate with benzaldehyde regioselectively afforded a mixture of the corresponding aldol and its dehydration product. The reactions of the title ketone with NBS, as well as of the silyl enol ethers derived therefrom with I-2, led to formation of mixtures of products via opening of the cyclopropane ring.

引用

页码：1234 / 1239

页数：6

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