Synthesis of optically active polycyclic compounds by Diels-Alder reactions of (+)-nopadiene

Lucio Minuti, Aldo Taticchi, Assunta Marrocchi, Alessandra Broggi, Eszter Gacs-Baitz

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

4-Oxo-2-cyclopentenylacetate 1 underwent a tandem Diels-Alder reaction with (+)-nopadiene 3 to lead to C 2-symmetric optically active polycyclic ketone 4. All attempts to carry out similar processes with acetoxy ketone 1 and two different dienes, that is, (+)-nopadiene 3 and isoprene 6 or 2,3-dimethyl-1,3-butadiene 7 were unsuccessful. Enantiomerically pure polycyclic ketones 8 and 9 were prepared by Diels-Alder cycloaddition between optically active α,β-unsaturated ketone 5 and dienes 6 and 7.

Original languageEnglish
Pages (from-to)3245-3248
Number of pages4
JournalTetrahedron Asymmetry
Volume15
Issue number20
DOIs
Publication statusPublished - Oct 18 2004

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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