DOI: 10.1039/A706802F
(Paper)
Reference Section for: Chem. Commun., 1997, 2395-2396
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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Masakatsu Matsumoto, Nobuko Watanabe, Akio Ishikawa and Hiroyuki Murakami
Abstract
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.
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