Reactive dienes: Intramolecular aromatic oxidation of 3-(2-hydroxyphenyl)-propionic acids

Organic Letters

Volumn 4, Issue 4, 2002, Pages 493-496

  Drutu, Ioana ^a   Njardarson, Jón T ^a   Wood, John L ^a  

^a YALE UNIVERSITY   (United States)

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ARTICLE;

EID: 0001677413     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0169776     Document Type: Article

References (23)

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6. For a review on the chemistry of orthoquinone monoketals and their orthoquinol analogues, see: Quideau, S.; Pouysegu, L. Org. Prep. Proced. Int. 1999, 31, 617.
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11. The structure was confirmed by preliminary single-crystal X-ray analysis.
12. Auksi, H.; Yates, P. Can. J. Chem. 1981, 59, 2510.
13. For a detailed discussion concerning the behavior of masked o-benzoquinones in normal and inverse electronic demand Diels-Alder reaction and possible FMO explanations, see: Liao, C. C.; Chu, C. S.; Lee, T. H.; Rao, P. D.; Ko, S.; Song, L. D.; Shiao, H. C. J. Org. Chem. 1999, 64, 4102.
14. (a) Holmberg, K. Acta Chem. Scand. 1974, B28, 857.
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16. Readily available from commercial starting materials. For experimental details see Supporting Information.
17. 3CN. A solution of BTIB (0.3 mmol, 1.2 equiv) was added, and the reaction mixture was allowed to stir overnight. The solvent was evaporated, and the residue was purified by flash chromatography on silicagel. For details, see Supporting Information.
18. 3SnH, confirming that the regio- and stereochemistry of addition are not affected by substitution.
19. 3CN, and the reaction was heated to 60°C. A solution of BTIB (0.3 mmol, 1.2 equiv) was added over 4 h (via syringe pump), and the reaction mixture was allowed to stir overnight at 60°C. The reaction was cooled to room temperature, the solvent was evaporated under reduced pressure, and the residue was purified by flash chromatography on silicagel. For details, see Supporting Information.
20. (a) Gao, S. Y.; Ko, S.; Lin, Y. L.; Peddinti, R. K.; Liao, C. C. Tetrahedron 2001, 57, 297.
21. (b) Arjona, O.; Mendel, R.; Plumet, J. Tetrahedron Lett. 1999, 40, 8431.
22. 3 (200 mg) was added, followed (after 5 min) by the dienophile (2.5-12.5 mmol, 10-50 equiv), and the reaction was allowed . to stir overnight. The solvent was evaporated, and the residue was purified by flash chromatography on silicagel. For details, see Supporting Information.
23. 1H NMR experiments and previous reports on similar systems (see ref 14).