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FORMATION OF A TRANS-BICYCLO[3.3.0]OCTANE BY TANDEM ANIONIC CYCLIZATION - EVIDENCE FOR THE HIGHLY STEREOSELECTIVE IRREVERSIBLE NATURE OF 5-HEXEN-1-YLLITHIUM CYCLIZATIONS

被引：36
作者：
BAILEY, WF
KHANOLKAR, AD
机构：
[1] Department of Chemistry, University of Connecticut, Storrs
来源：
TETRAHEDRON LETTERS | 1990年 / 31卷 / 42期
关键词：
D O I：
10.1016/S0040-4039(00)98011-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tandem anionic cyclization of 4-ethenyl-6-hepten-1-yllithium (7), prepared from the corresponding iodide (6) by low - temperature lithium - iodine exchange, occurs rapidly at room temperature in the presence of TMEDA to give (trans-3-bicyclo[3.3.0]octyl)methytlithium (9). Hydrolysis of the reaction mixture delivers 3-methyl-trans-bicyclo[3.3.0]octane in 87% yield. © 1990.
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页码：5993 / 5996
页数：4
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