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Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (05): 727-729. Previous Articles     Next Articles

Reports

(5R,6R)-6-苯基-5-(苯磺酰基乙酰基)二环[2.2.1]-2-庚烯的合成及结构表征

裴文*，孙莉，王海滨，王永江，邵越水   

  1. (浙江工业大学化学工程与材料学院 杭州 310014)
  • 收稿日期:2005-01-27 修回日期:2005-11-28 发布日期:2006-04-28
  • 通讯作者: 裴文

Synthesis and Characterization of (5R,6R)-6-Phenyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene

PEI Wen*,SUN Li,WANG Hai-Bin,WANG Yong-Jiang,SHAO Yue-Shui   

  1. (College of Chemical Engineering and Materials, Zhejiang University of Technology, Hangzhou 310014)
  • Received:2005-01-27 Revised:2005-11-28 Published:2006-04-28
  • Contact: PEI Wen

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A new method for preparation of 4-phenyl-1-phenylsulfonyl-3-butene-2-one was developed. 1-Bromo-4-phenyl-3-butene-2-one was obtained by the bromination of 4-phenyl-3-butene-2-one with , then reacted with sodium benzene sulfinate directly to give 4-phenyl- 1-phenylsulfonyl-3-butene-2-one in good yield. (5R,6R)-6-Phenyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]- hept-2-ene with＞99% ee was obtained by the asymmetric Diels-Alder reaction of 4-phenyl-1-phenylsulfonyl-3-butene-2-one with cyclopentadiene catalyzed by chiral titanium reagent. The asymmetric reaction mechanism was discussed and the adduct was characterized by X-ray, IR, MS and NMR spectra.

Key words: Diels-Alder reaction, synthesis, crystal structure, phenylsulfonyl unsaturated ketone, mechanism, asymmetric catalysis