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
收藏
页码：1234 / 1239
页数：6
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