Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one

Barbara Cardillo, Roberta Galeazzi, Giovanna Mobbili, Mario Orena, Monica Rossetti

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

By Swern oxidation of the hydroxamic acid 3, prepared from the homochiral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obtained, and its cycloaddition to either cyclohexadiene or cyclopentadiene proceeds with high diastereoselection, owing to the conformational stability of 4. The stereochemical outcome of the reaction is determined from 1H NMR data and further confirmed by the specific rotation value of 7, obtained by cleavage of the major cycloadduct 5a.

Original languageEnglish
Pages (from-to)1535-1540
Number of pages6
JournalTetrahedron: Asymmetry
Volume5
Issue number8
DOIs
Publication statusPublished - 1994

Fingerprint

nitroso compounds
Nitroso Compounds
Hydroxamic Acids
Cyclopentanes
Cycloaddition
Cycloaddition Reaction
cycloaddition
cleavage
Nuclear magnetic resonance
Derivatives
Oxidation
nuclear magnetic resonance
oxidation
acids
Acids
1,4-cyclohexadiene
ethylene urea
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

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

Cite this

Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one. / Cardillo, Barbara; Galeazzi, Roberta; Mobbili, Giovanna; Orena, Mario; Rossetti, Monica.

In: Tetrahedron: Asymmetry, Vol. 5, No. 8, 1994, p. 1535-1540.

Research output: Contribution to journalArticle

Cardillo, Barbara ; Galeazzi, Roberta ; Mobbili, Giovanna ; Orena, Mario ; Rossetti, Monica. / Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one. In: Tetrahedron: Asymmetry. 1994 ; Vol. 5, No. 8. pp. 1535-1540.
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