Chin. J. Org. Chem. ›› 2001, Vol. 21 ›› Issue (10): 728-731. Previous Articles     Next Articles

氨基醇砌块用于螺/环丙环类手性化合物的合成

王建平;陈庆华   

  1. 洛阳师范学院化学系;北京师范大学化学系.北京(100875)
  • 发布日期:2001-10-25

Application of amino alcohol as chiral building block in synthesis of spiro-cyclopropane derivatives containing multiple stereogenic centers

Wang Jianping;Chen Qinghua   

  1. Beijing Normal Univ., Dept of Chem..Beijing(100875)
  • Published:2001-10-25

The unusual, functionalized spiro-cyclopropane derivatives 7 containing four stereogenic centers were obtained in good yields with de≥98% via tandem double Michael addition/internal nucleophilic substitution of the chiral synthon, 5-l-menthyloxy-3-bromo-2-(5H)- furanone(4), with amino alcohol as chiral building block 3 under mild conditions. The novel chiral compounds 7 were identified on the basis of their analytcal data and spectroscopic data, such as UV, IR, ^1H NMR, ^13C NMR, MS and elementary analysis. This result can provide importnat synthetic strategy in synthesis of some complex molecules containing spiro-cyclopropane skeleton with multiple chiral centers.

Key words: AMINO ALCOHOL P, MICHAEL ADDITION REACTION, NUCLEOPHILIC REACTION, BLOCK, SPIRO COMPOUNDS, CYCLOPROPANE P, CHIRAL REAGENT, SYNTHESIS

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