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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (02): 240-245. 上一篇    下一篇

研究论文

铟参与的4-溴-1,1,1-三氟-2-丁烯与α-烷氧基醛亚胺的烯丙化反应: 4,4,4-三氟-γ-羟基缬氨酸的合成

陈盛a，陈琦b，卿凤翎*,a,b   

  1. (a东华大学生命科学和技术研究所 上海 201620)
    (b中国科学院上海有机化学研究所有机氟化学重点实验室 上海 200032)
  • 收稿日期:2006-09-21 修回日期:2006-11-01 发布日期:2007-01-30
  • 通讯作者: 卿凤翎

Indium-Mediated Diastereoselective Allylation of α-Alkoxy-aldimines with 4-Bromo-1,1,1-trifluoro-2-butene: Concise Synthesis of the Corresponding Lactone of 4,4,4-Trifluoro-γ-hydroxyvaline

CHEN Shenga, CHEN Qib, QING Feng-Ling*,a,b   

  1. (a Institute of Biological Sciences and Biotechnology, Donghua University, Shanghai 201620)
    (b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2006-09-21 Revised:2006-11-01 Published:2007-01-30
  • Contact: QING Feng-Ling

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铟参与的4-溴-1,1,1-三氟-2-丁烯与α-烷氧基醛亚胺的烯丙化反应以中等的产率和高非对映选择性生成了高烯丙基胺3. 从甘油醛亚胺和4-溴-1,1,1-三氟-2-丁烯反应制备的高烯丙基胺3g出发, 以7步反应24%的总产率合成了4,4,4-三 氟-γ-羟基缬氨酸11.

关键词: 铟, 三氟甲基氨基酸, 烯丙化反应

ndium-mediated allylation of α-alkoxy-aldimines with 4-bromo-1,1,1-trifluoro-2-butene gave the corresponding homoallylic amines 3 in moderate yield and high diastereoselectivity. Starting from compound 3g prepared by glyceraldimine with 4-bromo-1,1,1-trifluoro-2-butene in the presence of indium, compound 11, the corresponding lactone of (2R,3R)-4,4,4-trifluoro-γ-hydroxyvaline, was conveniently synthesized via 7 steps in 24% overall yield.

Key words: indium, diastereoselective allylation, trifluoromethylated amino acid