Stereocomplementary construction of 2-ethynyl-3-hydroxytetrahydrofuran derivatives via endo-mode ring closure of 3,4-epoxy-6-substitutedhex-5-yn-1-ols

Stereocomplementary construction of 2-ethynyl-3-hydroxytetrahydrofuran derivatives via endo-mode ring closure of 3,4-epoxy-6-substitutedhex-5-yn-1-ols
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通过3,4-环氧-6-取代的己-5-yn-1-醇的内模式闭环立体互补构建2-乙炔基-3-羟基四氢呋喃衍生物

DOI:
10.1039/c39940001161
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发表时间:
1994
期刊:
Journal of The Chemical Society, Chemical Communications
影响因子:
--
通讯作者:
M. Hanaoka
M. Hanaoka
中科院分区:
--
文献类型:
--
作者:
C. Mukai;Y. Sugimoto;Y. Ikeda;M. Hanaoka

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3,4-环氧-6-取代己-5-炔-1-醇经BF_3·OEt_2处理后,得到的内模式环化产物的立体化学发生了反转,而环氧化物转化为相应的六羰基二钴配合物后,再经Lewis酸处理,得到的内模式环化产物的立体中心构型保持不变。
Treatment of 3,4-epoxy-6-substitutedhex-5-yn-1-ols with BF3·OEt2 gave the endo-mode cyclization products with inversion of stereochemistry, whereas conversion of the epoxides to the corresponding hexacarbonyldicobalt complexes, followed by Lewis-acid treatment provided the endo-mode products with retention of configuration at the newly formed stereogenic centre.