Stereoselective synthesis of (Z)-fluoroalkenes directed to peptide isosteres:: copper mediated reaction of trialkylaluminum with 4,4-difluoro-5-hydroxyallylic alcohol derivatives
Stereoselective synthesis of (Z)-fluoroalkenes directed to peptide isosteres:: copper mediated reaction of trialkylaluminum with 4,4-difluoro-5-hydroxyallylic alcohol derivatives
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DOI：
10.1016/j.tet.2005.04.034
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发表时间：
2005-06-13
期刊：
影响因子：
2.1
通讯作者：
Taguchi, T
中科院分区：
文献类型：
--
作者：
Nakamura, Y;Okada, M;Taguchi, T
铜催化的三烷基铝(R3Al)与(E)-4，4-二氟-5-羟基烯丙醇衍生物的烷基转移反应顺利进行，以完全Z和2，5-syn选择性的方式得到相应的2-烷基4-氟-5-羟基烯丙醇衍生物。这样得到的氟烯烃的C5-羟基通过一锅甲基化和叠氮化反应可以实现区域和立体选择性地转化为氨基。(C)2005爱思唯尔有限公司。保留所有权利。
Copper mediated alkyl-transfer reaction of trialkylaluminum (R3Al) with (E)-4,4-difluoro-5-hydroxyallylic alcohol derivative smoothly proceeded to give the corresponding 2-alkylated 4-fluoro-5-hydroxyhomoallylic alcohol derivative with completely Z and 2,5-syn selective manner. Regio- and stereoselective conversion of the C5-hydroxyl group of the fluoroolefin thus obtained to amino group could be achieved through one-pot mesylation and azidation reaction. (c) 2005 Elsevier Ltd. All rights reserved.