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Aza-Diels-Alder versus 1,3-Dipolar Cycloadditions of Methyl Glyoxylate Oxime with Cyclopentadiene
- Source :
- Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela, instname
- Publication Year :
- 2008
- Publisher :
- MDPI, 2008.
-
Abstract
- The 12th International Electronic Conference on Synthetic Organic Chemistry session Computational Chemistry The acid-catalyzed [3+2] and [4+2] cycloadditions between methyl glyoxylate oxime (1) and cyclopentadiene were investigated using various Lewis and/or Bronsted acids at different temperatures in dichloromethane as solvent. Besides the expected new adducts, (±)-methyl [(3-exo)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylate (2) and (±)-methyl [(3-endo)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylate (3) a third addict, (±) methyl (1R,4R,5R)-(2-ox-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate (4), whose formation can be explained by a concerted 1,3-dipolar cycloaddition, was obtained. Yields and product ratios were found to be more dependent on the catalyst than on the temperature; these results and the stereochemistry of the adducts, confirmed by spectroscopic data (1H and 13C NMR) and by X-ray cycloadditions This work was supported by Centro de Investigação em Química of University of Porto. The authors thank the Fundação para a Ciência e Tecnologia (FCT) for financial support of this work under project POCTI/QUI/44471/2002 (Pluri-annual and Programmatic Funding) and for the grant to C. A. D. Sousa (SFRH/BD/31526/2006)
- Subjects :
- Cyclopentadiene
Oxime
Medicinal chemistry
Cycloaddition
Adduct
chemistry.chemical_compound
chemistry
Glyoxylate oxiame
1,3-dipolar cycloaddition
1,3-Dipolar cycloaddition
Aza-Diels–Alder reaction
Aza-Diels-Alder reaction
Isoxazolidines
2-hydroxy-2-azabicyclo[2.2.1]heptenes
Brønsted–Lowry acid–base theory
Dichloromethane
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Journal :
- Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela, instname
- Accession number :
- edsair.doi.dedup.....b119de35963780c27cb1e06bba9bf78d