Practical synthesis and highly diastereoselective diels-alder reactions of 1-alkylthio-3-silyloxybutadienes

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 6406-6409

  Holmes, Janice M ^a   Albert, Andrea L ^a   Gravel, Michel ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CYCLOADDUCTS; DIASTEREOSELECTIVE; DIELS-ALDER REACTION; HIGH YIELD; THIOESTERS;

OLEFINS; SILANES;

CHEMICAL REACTIONS;

1 THIO 3 SILYLOXYBUTADIENE; ACID; ALKADIENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 70349131589     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901347u     Document Type: Article

References (22)

1. (a) Diels, O.; Alder, K Liebigs Ann. Chem. 1928, 460, 98-122.
2. For selected reviews, see: (b) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667.
3. (c) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
4. Danishefsky, S.; Kitahara, T. J. Am. Chem. Soc. 1974, 96, 7807-7808.
5. (a) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252-5253.
6. (b) Kozmin, S. A.; Green, M. T.; Rawal, V. H. J. Org. Chem. 1999, 64, 8045-8047.
7. Selected examples of 1-alkylthio- and 1-arylthio-1,3-butadienes: (a) Cohen, T.; Mura, A. J.; Shull, D. W.; Fogel, E. R.; Ruffner, R. J.; Falck, J. R. J. Org. Chem. 1976, 41, 3218-3219.
8. (b) Kozikowski, A. P.; Huie, E. J. Am. Chem. Soc. 1982, 104, 2923-2925.
9. (c) Overman, L. E.; Petty, C. B.; Ban, T.; Huang, G. T. J. Am. Chem. Soc. 1983, 105, 6335-6337.
10. (d) Grayson, J. I.; Warren, S.; Zaslona, A. T. J. Chem. Soc., Perkin Trans. 1 1987, 967-976.
11. (e) Pegram, J. J.; Anderson, C. B. Tetrahedron Lett. 1988, 29, 6719-6720.
12. (f) Skowrońska, A.; Dybowski, P.; Koprowski, M.; Krawczyk, E. Tetrahedron Lett. 1995, 36, 8133-8136.
13. (g) Maddaluno, J.; Gaonac'h, O.; Marcual, A.; Toupet, L.; Giessner-Prettre, C. J. Org. Chem. 1996, 61, 5290-5306.
14. (h) Olsen, R. K.; Shao, R.-l. J. Org. Chem. 1996, 61, 5852-5856.
15. Cyclic dienes derived from 2H-thiopyran-4-one were studied previously: (a) Ward, D. E.; Zoghaib, W. M.; Rhee, C. K. Tetrahedron Lett. 1990, 31, 845-848.
16. (b) Ward, D. E.; Gai, Y. Z.; Zoghaib, W. M. Can. J. Chem. 1991, 69, 1487-1497.
17. (c) Ward, D. E.; Gai, Y. Tetrahedron Lett. 1992, 33, 1851-1854.
18. (d) Ward, D. E.; Gai, Y. Can. J. Chem. 1992, 70, 2627-2634.
19. (e) Ward, D. E.; Nixey, T. E. Tetrahedron Lett. 1993, 34, 947-950.
20. (f) Ward, D. E.; Nixey, T. E.; Gai, Y.; Hrapchak, M. J.; Abaee, M. S. Can. J. Chem. 1996, 74, 1418-1436.
21. (g) Ward, D. E.; Gai, Y. Can. J. Chem. 1997, 75, 681-693.
22. Lastdrager, B.; Timmer, M. S. M.; van der Marel, G. A.; Overkleeft, H. S.; Overhand, M. J. Carbohydr. Chem. 2007, 26, 41-59.