Thermal and Lewis acid catalyzed diastereoselective intramolecular Diels-Alder reaction on α,β-unsaturated amides derived from (-)-8- aminomenthol

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5230-5236

  Andrés, Celia ^a   García Valverde, María ^a   Nieto, Javier ^a   Pedrosa, Rafael ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

8 AMINOMENTHOL; ALUMINUM CHLORIDE; AMIDE; BENZOXAZINE DERIVATIVE; HEXANE; MENTHOL; SOLVENT; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 0344848792     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9904462     Document Type: Article

References (59)

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3. For some reviews on IMDA reaction see: (a) Oppolzer, W. Heterocycles 1980, 14, 1615. (b) Brieger, G.; Bennet, J. N. Chem. Rev. 1980, 80, 63. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. Ciganek, E. Org. React. 1984, 32, 1. (e) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (f) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: New York, 1984. (g) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (h) Roush, W. R. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 5, p 513. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990. (j) Kappe, C. O.; Murphree, S. S. Tetrahedron 1997, 53, 14179.
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