Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles

Tsuyoshi Satoh, Mariko Miura, Ken Sakai, Yoshimi Yokoyama

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

Magnesium cyclopropylidene was generated from 1-chlorocyclopropyl phenyl sulfoxide with i-PrMgCl in THF at -78 °C in high yield by a sulfoxide-magnesium exchange reaction. The generated magnesium cyclopropylidene was found to be reactive with N-lithio arylamines to give α-amino-substituted cyclopropylmagnesiums. The reaction of the α-amino-substituted cyclopropylmagnesiums with several electrophiles was examined and a new method for a synthesis of cyclopropane amino acid derivatives was realized.

Original languageEnglish
Pages (from-to)4253-4261
Number of pages9
JournalTetrahedron
Volume62
Issue number17
DOIs
Publication statusPublished - Apr 24 2006

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this