One-step synthesis of optically active cyclic polyamines containing helicene

Shinobu Honzawa, Shinya Chiba, Hitoshi Okubo, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Chiral macrocyclic tetraamines containing four helicenes were effectively synthesized in one-step. Reductive coupling of a (P)- helicenedi(methylamine) and a (P)-helicenedicarbaldehyde gives a cyclic (P,P,P,P)-tetramer in 88% yield. The (P,M,P,M)-diastereomer was effectively synthesized from the (M)-diamine and the (P)-dialdehyde in 66% yield. The intermediate (P,P,P,P)-imine and (P,M,P,M)-imine can be isolated also in high yields. The reductive coupling of achiral arenes, m-phenylenedi(methylamine) and m-phenylenedicarbaldehyde gives the cyclic tetramer in 47% yield, which is accompanied by the higher cyclic oligomers containing hexamer (18%) and octamer (3%). The condensed benzene ring system of the helicene appears to play an important role in the high yielding cyclic tetramerization.

Original languageEnglish
Pages (from-to)1091-1099
Number of pages9
JournalHeterocycles
Volume57
Issue number6
Publication statusPublished - 2002 Jun 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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