From a spin-off to the advantageous use in Diels-Alder reactions: A combined synthetic, spectroscopic and computational approach to N-(dienyl)acylamines

Organic and Biomolecular Chemistry

Volumn 2, Issue 6, 2004, Pages 845-851

  G̈rdes, Dirk ^a   Von Wangelin, Axel Jacobi ^a   Klaus, Stefan ^a   Neumann, Helfried ^a   Strübing, Dirk ^a   Hübner, Sandra ^a   Jiao, Haijun ^a   Baumann, Wolfgang ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; ALDEHYDES; CATALYSIS; COMPUTATIONAL METHODS; CONDENSATION REACTIONS; PYROLYSIS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CURTIUS REARRANGEMENT; DIELS-ALDER REACTIONS;

AMINES;

BETULACEAE;

EID: 1842430022     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b316026b     Document Type: Article

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37. All geometries were first optimized at the ab initio HF/3-21G level of theory and then refined at the B3LYP/6-31G(d) density functional level of theory. Optimized stationary points on the potential energy surface were characterized as energy minima with only real frequencies order, transition state with only one imaginary frequency at the HF/3-21G level. This frequency calculation provides also the zero-point energies (ZPE, scaled by 0.89) for correcting the calculated relative energies. The final energies for discussion are the single-point energies at the B3LYP/6-311+G(d,p) level with the B3LYP/6-31G(d) geometries, including the ZPE corrections. All calculations were performed using the Gaussian 98 program. For further details, see Supporting Information of ref. 8a.
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41. Although thermodynamics favor isopropyl-substituted aminodiene 3 in its 1Z-isomeric form, multicomponent Diels-Alder additions to maleimide resulted in the exclusive formation of the all-syn product, thus testifying to the kinetic preference for the 1E-aminodiene. See also ref. 8a.
42. 13C NMR experiments were performed at 25°C. For details, see Experimental section.