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  • 标题:Asymmetric N–H Insertion Reaction with Chiral Aminoalcohol as Catalytic Core of Cinchona Alkaloids
  • 本地全文:下载
  • 作者:Hideyuki Shinohara ; Hiroaki Saito ; Taketo Uchiyama
  • 期刊名称:Chemical and Pharmaceutical Bulletin
  • 印刷版ISSN:0009-2363
  • 电子版ISSN:1347-5223
  • 出版年度:2019
  • 卷号:67
  • 期号:4
  • 页码:393-396
  • DOI:10.1248/cpb.c18-00795
  • 出版社:The Pharmaceutical Society of Japan
  • 摘要:In order to develop an efficient organocatalyst for the enantioselective N–H insertion reaction via carbene/carbenoid, the catalytic core of the cinchona alkaloids was investigated. According to our working hypothesis of an eight-membered ring transition state in the N–H insertion reaction, two pairs of enantiomers related to 2-amino-1-phenylethanol were investigated for their chiral inducing potential. Since both (1 R ,2 S )-isomers gave the N -phenyl-1-phenylglycine derivative enriched in the R -form, while their enantiomers gave the S -form, the 2-amino-1-phenylethanol structure is concluded to be the catalytic core of the cinchona alkaloid in the enantioselective N–H insertion reaction via rhodium(II) carbenoid.
  • 关键词:N–H insertion reaction;carbenoid;cooperative catalysis;organocatalyst;aminoalcohol
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