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

被引：11

作者：

Matsumoto, M ^{[1
]}

Watanabe, N ^{[1
]}

Ishikawa, A ^{[1
]}

Murakami, H ^{[1
]}

机构：

[1] Kanagawa Univ, Dept Mat Sci, Kanagawa 25912, Japan

来源：

CHEMICAL COMMUNICATIONS | 1997年 / 24期

关键词：

D O I：

10.1039/a706802f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 (BuOK)-O-t in DMSO at room temperature, whereas LDA-THF induces the cyclization of 1 to afford predominantly the stereoisomer cis-2.

引用

页码：2395 / 2396

页数：2

共 7 条

[1]

BIELLMANN JF, 1982, ORG REACTIONS, V27, P1

[2] ETHER CLEAVAGE WITH ORGANO-ALKALI-METAL COMPOUNDS AND ALKALI-METALS [J].