RT Book,_Section
T1 Aza-Diels-Alder versus 1,3-Dipolar Cycloadditions of Methyl Glyoxylate Oxime with Cyclopentadiene
A1 Sousa, Carlos A.D.
A1 Vale, M. Luísa C.
A1 Rodríguez Borges, José E.
A1 García Mera, Xerardo
K1 Aza-Diels-Alder reaction
K1 1,3-dipolar cycloaddition
K1 Glyoxylate oxiame
K1 Isoxazolidines
K1 2-hydroxy-2-azabicyclo[2.2.1]heptenes
AB 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
PB MDPI
SN 3-906980-20-0
YR 2008
FD 2008
LK http://hdl.handle.net/10347/26839
UL http://hdl.handle.net/10347/26839
LA eng
NO Sousa, 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-12-01218
NO The 12th International Electronic Conference on Synthetic Organic Chemistry session Computational Chemistry
NO 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)
DS Minerva
RD 3 may 2026