Alkylation-annulation of halo esters with organometallic reagent/SmI2 couple leading to cycloalkanols: A facile cyclopropanol synthesis from a 3-halo ester
作者:Shin-ichi Fukuzawa、Hideki Furuya、Teruhisa Tsuchimoto
DOI:10.1016/0040-4020(95)01039-4
日期:1996.2
Transformation of a 3-halo ester to cyclopropanols has been accomplished in excellent yields under mild conditions employing a coupled reagent of samarium(II) diiodide with organometallic reagents. 5- and 6- Halo esters were also transformed into cyclopentanols and cyclohexanols, respectively, in low to moderate yields. The reaction with a 4-halo ester gave 2,2-disubstituted tetrahydrofuran as a major
使用卤化二碘化((II)与有机金属试剂的偶联剂,在温和的条件下,以优异的收率将3-卤代酯转化为环丙醇。5-和6-卤代酯也分别以低到中等的产率转化成环戊醇和环己醇。与4-卤代酯的反应产生了2,2-二取代的四氢呋喃,其为主要产物,其是通过双烷基化然后环化而得到的。生成的取代环丁醇收率不高。