CYCLIZATION OF (4-METHOXY-5-HEXENYL)LITHIUM

被引：13

作者：

BAILEY, WF

JIANG, XL

机构：

[1] Department of Chemistry, University of Connecticut, Connecticut 06269-3060, Storrs

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 22期

关键词：

D O I：

10.1021/jo00101a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclization of (4-methoxy-5-hexenyl)lithium (1), which was prepared by lithium-iodine exchange between 3-methoxy-6-iodo-1-hexene (2) and 1.75 molar equiv of t-BuLi in diethyl ether-n-pentane solution at -78 degrees C, has been investigated in a variety of solvent systems. The isomeric composition of the cis- and trans-1-methoxy-2-methylcyclopentane produced upon cyclization of 1 followed by quench with MeOH has been found to be dramatically dependent on the solvent system in which the isomerization is conducted.

引用

页码：6528 / 6533

页数：6

共 49 条

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[42] ASYMMETRIC SYNTHESIS OF LOGANIN - STEREOSPECIFIC FORMATION OF "(1R,2R)-2-METHYL-3-CYCLOPENTEN-1-OL AND "(1S,2S)-2-METHYL-3-CYCLOPENTEN-1-OL AND (2R)-2-METHYLCYCLOPENTANONE AND (2S)-2-METHYLCYCLOPENTANONE [J].