Selected Paper : Unexplored Reactivity of N-Alkyl Unsaturated Imines : A Simple Procedure for Producing Optically Active 1,3-Diamines via a Stereocontrolled Formal [4+2] and [4+2+2] Iminocycloaddition

• Ambara R. Pradipta

• Katsunori Tanaka

抄録

Imines are among the most ubiquitous species in organic and bioorganic chemistry; however, the reactivities of N-alkyl unsaturated imines have not been thoroughly explored due to their instability profiles. Here, we describe the novel reactivity of N-alkyl unsaturated imines derived from substituted aldehydes, a chiral aminoalcohol, and paraformaldehyde to produce hexahydropyrimidines and 1,3,5-triazacyclooctanes through a formal asymmetric [4+2] and [4+2+2] cycloaddition reaction in a stereocontrolled manner. The reaction products were successfully transformed via simple functional group manipulations to the variously substituted chiral 1,3-diamines, which could not be simply accessed by other methods.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 89 (3), 337-345, 2016-03

  Tokyo : Chemical Society of Japan

キーワード

• General Chemistry

詳細情報

• CRID: 1520010381007965824
• NII論文ID: 130005137572
• NII書誌ID: AA00580132
• ISSN: 00092673
• ISSN: 13480634
• DOI: 10.1246/bcsj.20150358
• NDL書誌ID: 027165350
• Web Site: http://id.ndl.go.jp/bib/027165350
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I027165350
• Web Site: https://academic.oup.com/bcsj/article-pdf/89/3/337/56278745/bcsj.20150358.pdf
• 本文言語コード: en
• NDL 雑誌分類:
  • ZP1(科学技術--化学・化学工業)
• データソース種別:
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN