Absolute Configuration of 2‐Substituted 2‐Azabicyclo[2.2.1]hept‐5‐enes
- 12 May 1993
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 76 (3) , 1203-1215
- https://doi.org/10.1002/hlca.19930760307
Abstract
The diastereoisomeric 2‐substituted 2‐azabicyclo[2.2.1]hept‐5‐enes 2–4 were prepared by aza‐Diels‐Alder reaction of cyclopentadiene with the corresponding methaniminium ions. Their relative configurations were deduced using 1H, 1H‐ROESY experiments, and their absolute configurations were assigned from the crystal structure of the aziridinium derivative (−)‐5. The absolute configuration of (+)‐1, i.e. (1R), was assigned by CD spectroscopy.Keywords
This publication has 26 references indexed in Scilit:
- Asymmetrische Aza‐Diels‐Alder‐ReaktionenNachrichten aus Chemie, Technik und Laboratorium, 1992
- Asymmetric aza-Diels-Alder reaction mediated by chiral boron reagentThe Journal of Organic Chemistry, 1992
- Initial-state and transition-state effects on Diels-Alder reactions in water and mixed aqueous solventsJournal of the American Chemical Society, 1992
- Asymmetric synthesis of bicyclic amino acid derivatives by Aza‐Diels‐Alder reactions in aqueous solutionEuropean Journal of Organic Chemistry, 1991
- Diels-Alder reactions in aqueous solutions. Enforced hydrophobic interactions between diene and dienophileJournal of the American Chemical Society, 1991
- Rapid-pulsing artifacts in double-quantum-filtered COSYJournal of Magnetic Resonance (1969), 1990
- Frequency offset effects and their elimination in NMR rotating-frame cross-relaxation spectroscopyJournal of Magnetic Resonance (1969), 1987
- Optically active amines. 32. Far ultraviolet circular dichroism observations on the substituted benzene chromophoreJournal of the American Chemical Society, 1987
- Sensitivity-enhanced two-dimensional heteronuclear shift correlation NMR spectroscopyJournal of Magnetic Resonance (1969), 1986
- Circular dichroism of an optically active olefin chromophore: (R)-3-methylcyclopenteneJournal of the American Chemical Society, 1980