The first catalytic inverse-electron demand hetero-Diels-Alder reaction of nitroso alkenes using pyrrolidine as an organocatalyst

Organic and Biomolecular Chemistry

Volumn 2, Issue 6, 2004, Pages 828-834

  Wabnitz, Tobias C ^a   Saaby, Steen ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CATALYSTS; COLUMN CHROMATOGRAPHY; ESTERS; HYDROLYSIS; LIQUID CHROMATOGRAPHY; POLYMERIZATION; REACTION KINETICS; STEREOCHEMISTRY;

CYCLOADDITION; HETERO-DIELS-ALDER REACTION;

OLEFINS;

BETULACEAE;

EID: 1842586980     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b316518c     Document Type: Article

References (43)

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30. An analogous reaction took also place with α-chloroacetophenone oxime (2b).
31. The use of homogeneous bases such as triethylamine or Hünig's base led to immediate decomposition of the halooxime.
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34. Protic solvents such as ethanol cannot be used as they undergo conjugate addition reactions to nitroso alkenes.
35. These stark differences in reactivity of O-alkylated and nonalkylated oximes have been noticed previously, see: H. C. J. Ottenheijm, R. Plate, J. H. Noordik and J. D. M. Herscheid, J. Org. Chem., 1982, 47, 2147-2154.
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42. Hemiacetal diastereomers could not be separated in any case and rapid equilibration via an open chain aldehyde intermediate is likely.
43. Small quantities of the chlorooxime 7b were formed through halide exchange during this procedure and could not be separated from the product.