Synthesis of enantiopure angularly condensed [2.2]paracyclophanes containing five-membered rings

Lucio Minuti, Aldo Taticchi, Assunta Marrocchi, Daniela Lanari, Alessandra Broggi, E. Gács-Baitz

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Optically active angularly condensed [2.2]paracyclophanes containing five-membered rings have been synthesized by a two-step approach based on the Diels-Alder cycloaddition of (S)-(+)-4-vinyl[2.2]paracyclophane. Structural analysis by NMR spectroscopy is presented. These helicenophanes containing a cyclopentane ring show extraordinarily high specific rotations. This phenomenon has been discussed in terms of structural modifications caused by the replacement of the benzene unit with a cyclopentane ring.

Original languageEnglish
Pages (from-to)481-487
Number of pages7
JournalTetrahedron Asymmetry
Volume14
Issue number4
DOIs
Publication statusPublished - Feb 21 2003

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Cyclopentanes
Cycloaddition
Structural analysis
Nuclear magnetic resonance spectroscopy
Benzene
rings
Cycloaddition Reaction
synthesis
Magnetic Resonance Spectroscopy
cycloaddition
structural analysis
benzene
nuclear magnetic resonance
spectroscopy
(2.2)paracyclophane

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Synthesis of enantiopure angularly condensed [2.2]paracyclophanes containing five-membered rings. / Minuti, Lucio; Taticchi, Aldo; Marrocchi, Assunta; Lanari, Daniela; Broggi, Alessandra; Gács-Baitz, E.

In: Tetrahedron Asymmetry, Vol. 14, No. 4, 21.02.2003, p. 481-487.

Research output: Contribution to journalArticle

Minuti, Lucio ; Taticchi, Aldo ; Marrocchi, Assunta ; Lanari, Daniela ; Broggi, Alessandra ; Gács-Baitz, E. / Synthesis of enantiopure angularly condensed [2.2]paracyclophanes containing five-membered rings. In: Tetrahedron Asymmetry. 2003 ; Vol. 14, No. 4. pp. 481-487.
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