One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the n-tosyl imine of chloroacetaldehyde with an asymmetric mannich reaction as a key step

Yujiro Hayashi, Tatsuya Urushima, Daisuke Sakamoto, Kou Torii, Hayato Ishikawa

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Aziridines with ease: A one-pot synthesis of chiral aziridine derivatives with excellent diastereo- and enantioselectivities was developed through uninterrupted sequential reactions, including desulfonylative formation of the N-Ts imine derived from chloroacetaldehyde, a diarylprolinol silyl ether mediated asymmetric Mannich reaction, reduction, and aziridine formation (see scheme; Ts=tosyl).

Original languageEnglish
Pages (from-to)11715-11718
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number42
DOIs
Publication statusPublished - 2011 Oct 10
Externally publishedYes

Keywords

  • Mannich reaction
  • asymmetric reaction
  • domino reactions
  • enantioselectivity
  • one-pot reaction
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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