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有机化学 ›› 2008, Vol. 28 ›› Issue (06): 1119-1122. 上一篇    下一篇

研究简报

新型手性<i>β</i>-烷氨基-<i>γ</i>-(<i>l</i>-孟氧基)丁内酯的合成

郁兆莲，胡少强，李森兰，傅玉琴*   

  1. (洛阳师范学院化学化工学院 洛阳 471000)
  • 收稿日期:2007-09-28 修回日期:2007-12-19 发布日期:2008-06-26
  • 通讯作者: 傅玉琴

Synthesis of Novel <i>β</i>-Alkylamino-<i>γ</i>-(<i>l-</i>menthoxy)butyrolactones

YU Zhao-Lian, HU Shao-Qiang, LI Sen-Lan, FU Yu-Qin*   

  1. (<I>School of Chemistry and Chemical Engineering</i>,<i> Luoyang Normal University</i>,<i> Luoyang 471000</i>)
  • Received:2007-09-28 Revised:2007-12-19 Published:2008-06-26
  • Contact: FU Yu-Qin

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脂肪族伯胺作为亲核试剂与手性合成子5(<I>R</I>)-(<i>l</i>-孟氧基)-2(5H)-呋喃酮(<b>4</b>)发生不对称Michael加成反应, 得到一系列新的手性<i>β</i>-烷氨基-<i>γ</i>-(<i>l</i>-孟氧基)丁内酯类化合物<b>6</b>(产率34～81%, <i>de</i>≥98%). 通过IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, MS, 元素分析及单晶X射线衍射分析, 确认了它们的化学结构、立体化学和绝对构型. 此结果为某些具有生物活性化合物及复杂分子的合成提供了新的途径.

关键词: 单晶X射线衍射, #NAME?, 不对称合成, Michael加成, /i>, <, γ<, i>

A series of novel chiral <i>β</i>-alkylamino-<i>γ</i>-menthoxybutyrolactones <b>6</b> were synthesized in moderate to good yields (34%～81%) with high diastereoselectivity (<i>de</i>≥98%) via the asym-metric Michael addition of various primary amines to chiral synthon 5(<I>R</I>)-(<i>l</i>-menthoxy)-2,5-dihydrofuran-2-one (<b>4</b>) under mild conditions. The structure and absolute configuration of compounds <b>6</b> were established on the basis of their elemental analysis and spectroscopic data, such as IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, MS spectra, and sin-gle-crystal X-ray diffraction. These results provide a valuable synthetic route to some biologically active compounds and complex molecules.

Key words: <, /i>, i>, γ<, single-crystal X-ray diffraction, #NAME?, Michael addition, asymmetric synthesis