Base-induced cyclization of 1-benzyloxy-2,2,4,4-tetramethylpentan-3-ones: intramolecular nucleophilic addition of an anion of a benzyl ether to the carbonyl moiety without the Wittig rearrangement or protophilic decomposition
Base-induced cyclization of 1-benzyloxy-2,2,4,4-tetramethylpentan-3-ones: intramolecular nucleophilic addition of an anion of a benzyl ether to the carbonyl moiety without the Wittig rearrangement or protophilic decomposition
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碱诱导的 1-benzyloxy-2,2,4,4-tetramethylpentan-3-ones 环化：苄基醚阴离子与羰基部分发生分子内亲核加成，无需维蒂希重排或亲原分解
DOI：
10.1039/a706802f
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发表时间：
1997
影响因子：
4.9
通讯作者：
Hiroyuki Murakami
中科院分区：
文献类型：
--
作者：
M. Matsumoto;N. Watanabe;A. Ishikawa;Hiroyuki Murakami
在室温下，在DMSO中，含烷基链(1)上含有羰基部分的烷基苄基醚有效地环化，没有Wittig重排或原生分解，得到与ButOK处理的羟基四氢呋喃(tran-2)，而LDA-THF诱导1的环化反应得到主要的立体异构体顺式-2。
Alkyl benzyl ethers bearing a carbonyl moiety in the alkyl chain (1) cyclize effectively, without the Wittig rearrangement or protophilic decomposition, to give hydroxytetrahydrofurans (trans-2) on treatment with ButOK in DMSO at room temperature, whereas LDA–THF induces the cyclization of 1 to afford predominantly the stereoisomer cis-2.