Sousa, Carlos A.D.Vale, M. Luísa C.Rodríguez Borges, José E.García Mera, Xerardo2021-08-182021-08-182008Sousa, C.A.; Vale, M.C.; Rodríguez-Borges, J.E.; García-Mera, X. Aza-Diels-Alder versus 1,3-Dipolar Cycloadditions of Methyl Glyoxylate Oxime with Cyclopentadiene, in Proceedings of the 12th International Electronic Conference on Synthetic Organic Chemistry, 1–30 November 2008, MDPI: Basel, Switzerland, doi:10.3390/ecsoc-12-012183-906980-20-0http://hdl.handle.net/10347/26839The 12th International Electronic Conference on Synthetic Organic Chemistry session Computational ChemistryThe 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 cycloadditionseng© 2008 The author(s). Published by MDPI, Basel, Switzerland. Open AccessAza-Diels-Alder reaction1,3-dipolar cycloadditionGlyoxylate oxiameIsoxazolidines2-hydroxy-2-azabicyclo[2.2.1]heptenesbook part10.3390/ecsoc-12-01218open access