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Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (02): 240-245. Previous Articles     Next Articles

Original Articles

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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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