Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (06): 1119-1122. Previous Articles     Next Articles

Reports

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

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