Intramolecular Arylation Reactions of Alkenes: A Flexible Approach to Chromans and Tetrahydroquinoline Derivatives

Journal of the American Chemical Society

Volumn 126, Issue 11, 2004, Pages 3416-3417

  Barluenga, José ^a   Trincado, Mónica ^a   Rubio, Eduardo ^a   González, José M ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CHROMAN DERIVATIVE; HETEROCYCLIC COMPOUND; QUINOLINE DERIVATIVE; TETRAHYDROQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL BOND; CYCLIZATION; IODINATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 1642410363     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0397299     Document Type: Article

References (42)

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31. 1d and 1e are terminal alkenes that react in this process at reasonably fast rates. In sharp contrast to this trend, allylphenyl ether cannot be cyclized to the parent 3-iodochroman using this approach.
32. 2I.
33. The use of N-methyl-N-allylaniline as starting material did not result in the desired heterocycle. Protection of the secondary amines as sulfonyl derivatives provided satisfactory model compounds.
34. 13C), MS, and analytical data in good agreement with the proposed structures (see Supporting Information).
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37. The different availability of the lone pair of electrons onto the oxygen atom in ethers 1 compared to that onto nitrogen in sulfonamides 5 could argue in favor of differences observed between this two series.
38. 4, after reaction for 1 h at -85 °C, 32% of its isomer 1f was isolated from the crude reaction mixture.
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40. The regiochemistry is opposite to that in the palladium(0)-catalyzed cyclization of o-iodoaryl allyl ethers that gave substituted benzofurans, see: Larock, R. C.; Stinn, D. E. Tetrahedron Lett. 1988, 29, 4687.
41. These are new examples of the known preference for the formation of six-membered rings (6-endo-trig approach) over the related five-membered (5-exo-trig) in cationic-like cyclization of 1,5-dienes, see: (a) Sutherland, J. K. Chem. Soc. Rev. 1980, 9, 265. The noticed selectivity can be interpreted as a consequence of a cyclization taking place according to the Stork-Eschenmoser postulate:
42. (b) Barlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1984; Vol. 3, pp 341-409.