高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 60.

• Organic Synthesis Chemistry • 上一篇    下一篇

ASYMMETRIC ADDITION OF (+)-CAMPHOR SULFINIMINES WITH DIETHYLALUMINUM CYANIDE

Li Yan, Zhu Wei, Cheng Zhi-Yong, Yang Gui-Shu   

  1. Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy Of Sciences 610041
  • 出版日期:1998-12-31 发布日期:1998-12-31
  • 基金资助:
    National Natural Science Foundation of China (NNSFC) (No. 29772032) for financial support

ASYMMETRIC ADDITION OF (+)-CAMPHOR SULFINIMINES WITH DIETHYLALUMINUM CYANIDE

Li Yan, Zhu Wei, Cheng Zhi-Yong, Yang Gui-Shu   

  1. Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy Of Sciences 610041
  • Online:1998-12-31 Published:1998-12-31
  • Supported by:
    National Natural Science Foundation of China (NNSFC) (No. 29772032) for financial support

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摘要： The development of new and improved methods for the asymmetric synthesis of α-amino acids is of considerable current interest because of their importance in biological systems and their exceptional utility as chiral building blocks. Of the many methods used to prepare α-amino acids, the asymmetric Strecker synthesis should hold particular prominence because of its simplicity1. Recently, F. A. Davis and his coworkers reported that diethylaluminum cyanide (Et2AlCN) adds to enantiopure p-tolylsulfinimines to give α-sulfinamino nitriles at 82-84% diastereoselectivity. Treatment of α-sulfinamino nitriles with acid removes the chiral auxiliary p-tolylsulfinyl group and hydrolyzes the nitrile to give α-amino acids without epimerization2. This research was quoted in Highlight by Chemistry & Industry as an improved asymmetric Strecker synthesis3. However, the diastereoselectivity of this addition reaction needs to be improved more high, and moreover, the preparation of p-tolylsulfinimines from nonracemic p-tolylsulfinamides and aldehydes needs strong organic metallic bases2b, so it is desirable to design an easier prepared and effective optical sulfinimines.

Abstract: The development of new and improved methods for the asymmetric synthesis of α-amino acids is of considerable current interest because of their importance in biological systems and their exceptional utility as chiral building blocks. Of the many methods used to prepare α-amino acids, the asymmetric Strecker synthesis should hold particular prominence because of its simplicity1. Recently, F. A. Davis and his coworkers reported that diethylaluminum cyanide (Et2AlCN) adds to enantiopure p-tolylsulfinimines to give α-sulfinamino nitriles at 82-84% diastereoselectivity. Treatment of α-sulfinamino nitriles with acid removes the chiral auxiliary p-tolylsulfinyl group and hydrolyzes the nitrile to give α-amino acids without epimerization2. This research was quoted in Highlight by Chemistry & Industry as an improved asymmetric Strecker synthesis3. However, the diastereoselectivity of this addition reaction needs to be improved more high, and moreover, the preparation of p-tolylsulfinimines from nonracemic p-tolylsulfinamides and aldehydes needs strong organic metallic bases2b, so it is desirable to design an easier prepared and effective optical sulfinimines.

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