Reactivity studies of 3,3-bis(trimethylsilyl)-2-methyl-1-propene in Lewis acid-catalyzed allylation reactions.
Reactivity studies of 3,3-bis(trimethylsilyl)-2-methyl-1-propene in Lewis acid-catalyzed allylation reactions.
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DOI：
10.1021/ol0613160
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发表时间：
2006-09
期刊：
影响因子：
5.2
通讯作者：
David R. Williams;Ángel I. Morales-Ramos;C. M. Williams
中科院分区：
文献类型：
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作者：
David R. Williams;Ángel I. Morales-Ramos;C. M. Williams
具有双三甲基硅基取代的烯丙化试剂很容易从E-或Z-烯基溴化物中制备。描述了3，3-双(三甲基硅基)-2-甲基-1-丙烯(1)的反应性，并主要提供在BF3.OEt2存在下与醛反应得醇2。或者，通过在二氯甲烷中使用更强的Lewis酸来观察1的樱花烯丙基化反应，以唯一地生成E-三取代的烯基硅烷3。
Allylation reagents, which possess geminal bis-trimethylsilyl substitution, are readily prepared from E- or Z-alkenyl bromides. The reactivity of 3,3-bis(trimethylsilyl)-2-methyl-1-propene (1) is described and predominantly provides ene reactions with aldehydes to give alcohol 2 in the presence of BF3.OEt2. Alternatively, Sakurai allylation reactions of 1 are observed by using stronger Lewis acids in methylene chloride to exclusively yield E-trisubstituted alkenylsilanes 3.