Regioselective single and double conjugate additions to substituted cyclohexa-2,5-dienone monoacetals

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3167-3170

  Grecian, Scott ^a   Wrobleski, Aaron D ^a   Aubé, Jeffrey ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXADIENONE; CYCLOHEXANE DERIVATIVE; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BICYCLO COMPOUNDS, HETEROCYCLIC; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXANES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 23044465718     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050715c     Document Type: Article

References (21)

1. The terms "quinone monoacetal" and "quinone monoketal" may be used interchangeably. For a review of quinone monoacetal chemistry, see: Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383-1430.
2. For examples of conjugate additions to quinone monoacetals, see ref 1 and the following specific examples. (a) Chenard, B. L.; Anderson, D. K.; Swenton, J. S. J. Chem. Soc., Chem. Commun. 1980, 19, 932-933.
3. (b) Stern, A. J.; Swenton, J. S. J. Chem. Soc., Chem. Commun. 1988, 18, 1255-1256.
4. (c) Parker, K. A.; Casteel, D. A. J. Org. Chem. 1988, 53, 2847-2850.
5. (d) Stern, A. J.; Rohde, J. J.; Swenton, J. S. J. Org. Chem. 1989, 54, 4413-4419.
6. (e) Ciufolini, M. A.; Dong, Q.; Yates, M. H.; Schunk, S. Tetrahedron Lett. 1996, 37, 2881-2884.
7. (f) Högenauer, K.; Baumann, K.; Mulzer, J. Tetrahedron Lett. 2000, 41, 9229-9232.
8. For examples of conjugate additions to quinones containing electron-withdrawing groups, see: (a) Valderrama, J. A.; Cortes, M.; Pessoa-Mahana, D.; Preite, M.; Benites, J. Tetrahedron Lett. 2000, 41, 3563-3566.
9. (b) Valderrama, J. A.; Pessoa-Mahana, D.; Tapia, R. A.; Rojas de Arias, A.; Nakayama, H.; Torres, S.; Miret, J.; Ferreira, M. E. Tetrahedron 2001, 57, 8653-8658.
10. (c) Brimble, M. A.; Halim, R.; Petersson, M. Tetrahedron Lett. 2002, 43, 4777-5758.
11. (d) Brimble, M. A.; Burgess, C.; Halim, R.; Petersson, M.; Ray, J. Tetrahedron 2004, 60, 5751-5758.
12. (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992; Vol. 9, pp 1-8.
13. (b) Aponick, A.; Buzdygon, R. S.; Tomko, R. J., Jr.; Fazal, A. N.; Shughart, E. L.; McMaster, D. M.; Myers, M. C.; Pitcock, W. H., Jr.; Wigal, C. T. J. Org. Chem. 2002, 67, 242-244.
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16. (b) Camps, P.; Gonzalez, A.; Munoz-Torrero, D.; Simon, M.; Zuniga, A.; Martins, M. A.; Font-Bardia, M.; Solans, X. Tetrahedron 2000, 56, 8141-8151.
17. (c) Carreno, M. C.; Luzon, C. G.; Ribagorda, M. Chem. Eur. J. 2002, 8, 208-216.
18. Quinone monoacetals 1-4 were generally made by oxidation of the corresponding 4-alkoxy phenol. See Supporting Information for details.
19. Silva, P. C.; Costa, J. S.; Pereira, V. L. P. Synth. Commun. 2001, 31, 595-600.
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21. Danishefsky, S.; Schuda, P.; Kato, K. J. Org. Chem. 1976, 41, 1081-1088.