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Application of modified amino acid as a chiral building block in asymmetric synthesis
  • ISSN号:0438-0479
  • 期刊名称:《厦门大学学报:自然科学版》
  • 时间:0
  • 分类:O623[理学—有机化学;理学—化学]
  • 作者机构:[1]Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China, [2]Luoyang Teachers Coll, Dept Chem, Luoyang 471022, Peoples R China
  • 相关基金:This work was supported by the National Natural Science Foundation of China (Grant No. 29672004).
中文摘要:

Phenylglycine 1 as a representative of natural resourceful a-amino acid was modified by reduction and protection of functional group to afford the amino alcohol as a chiral building block 3. A new chiral compound, the chiral building block/spiro-cyclopropane derivative containing four stereogenic centers, compound 7, has been obtained in 52% yield with de≥98% via the tandem double Michael addition/internal nucleophilic substitution under mild condition of 5-l-menthyloxy-3-bromo-2-(5H)-furanone 4 with the nucleophilic reagent, the amino alcohol 3. The new chiral compound 7 is identified on the basis of its analytical data and spectroscopic data, such as UV, IR, 1H NMR, 13C NMR, MS and elementary analysis. The absolute configuration of the interesting spiro-cyclopropanes 7 was established by X-ray crystallography. This result can provide new route and method for the introduction of chiral building block and the important synthetic strategy in synthesis of some complex molecules containing spiro-cyclopropa

英文摘要:

Phenylglycine 1 as a representative of natural resourceful α-amino acid was modified by reduction and protection of functional group to afford the amino alcohol as a chiral building block 3. A new chiral compound, the chiral building block/spiro-cyclopropane derivative containing four stereogenic centers, compound 7, has been obtained in 52% yield with de?98% via the tandem double Michael addition/internal nucleophilic substitution under mild condition of 5-l-menthyloxy-3-bromo-2-(5H)-furanone 4 with the nucleophilic reagent, the amino alcohol 3. The new chiral compound 7 is identified on the basis of its analytical data and spectroscopic data, such as UV, IR,1H NMR,13C NMR, MS and elementary analysis. The absolute configuration of the interesting spiro-cyclopropanes 7 was established by X-ray crystallography. This result can provide new route and method for the introduction of chiral building block and the important synthetic strategy in synthesis of some complex molecules containing spiro-cyclopropane skeleton with multiple chiral centers and the study of their biological activity.

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期刊信息
  • 《厦门大学学报:自然科学版》
  • 中国科技核心期刊
  • 主管单位:中华人民共和国教育部
  • 主办单位:厦门大学
  • 主编:谢素原
  • 地址:厦门市思明南路422号厦门大学嘉庚三 817-819室
  • 邮编:361005
  • 邮箱:jxmu@xmu.edu.cn
  • 电话:0592-2180367 2187731
  • 国际标准刊号:ISSN:0438-0479
  • 国内统一刊号:ISSN:35-1070/N
  • 邮发代号:34-8
  • 获奖情况:
  • 多次被评为全国、华东地区、福建省的优秀科技期刊,2001年入选国家新闻出版总署评定的"中国期刊方阵",2003年获国家新闻出版总署颁发的"第二届国家科技...,2006年获国家教育部科技司颁发的"首届中国高校精...
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  • 被引量:16575