STEREOSELECTIVE SYNTHESES OF 1,2-DIALKYL-1-PHENYL-CYCLOPENTANES BY INTRAMOLECULAR CARBOLITHIATION OF VINYL SULFIDES

被引：16
|
作者：
KRIEF, A
KENDA, B
REMACLE, B
机构：
[1] Department of Chemistry. Facultés Universitaires Notre-Dame de la Paix, B-5000 NAMUR
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 43期
关键词：
D O I：
10.1016/0040-4039(95)01641-T
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
6-Methylseleno-6-phenyl-1-phenyithio-1-heptene and 7-methylseleno-7-phenyl-2-phenylthio-2-octene produce 1-phenyl-2-(1'-phenylthioethyl)-cyclopentanes with high stereocontrol at all the three stereogenic centers on sequential reaction with butyllithium and methyl iodide or methanol respectively. Depending upon the solvent used, the derivative in which the methyl- and the phenylthio group are cis (THF) or trans (pentane) one to the other are selectively formed.
引用
收藏
页码：7917 / 7920
页数：4
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