Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: Synthesis of 3-substituted azepanes

Journal of Organic Chemistry

Volumn 72, Issue 18, 2007, Pages 7050-7053

  Denmark, Scott E ^a   Xie, Min ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPANES; CONJUGATE ADDITION; LEWIS ACID; NITROALKENES;

ADDITION REACTIONS; OLEFINS; SILANES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ETHERS;

ALKENE DERIVATIVE; AZEPANE DERIVATIVE; HETEROCYCLIC COMPOUND; LEWIS ACID; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CONJUGATION; DESILYLATION; HYDROGENATION; REACTION TIME; REDUCTION; SYNTHESIS;

ACIDS; ALKENES; AZEPINES; ETHERS; MOLECULAR STRUCTURE; NITRO COMPOUNDS; SILANES;

EID: 34548804350     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071126i     Document Type: Article

References (27)

1. Proctor, G. R.; Redpath, J. Monocyclic Azepines: The Synthesis and Chemical Properties of the Monocyclic Azepines; John Wiley & Sons: New York, 1996.
2. Fernandez, F.; Perez, C. Heterocycles 1987, 26, 2411-2417.
3. Georg, G. I.; Guan, X.; Kant, J. Bioorg. Med. Chem. Lett. 1991, 1, 125-128.
4. Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9131-9166.
5. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.; Rusche. J. J. Prakt. Chem. 1977, 319, 195-200.
6. Newkome, G. R. Comprehensive Heterocyclic Chemistry II, Vol. 9: Seven Membered and Larger Rings and All Fused Derivatives; Pergamon: NewYork, 1996.
7. Barluenga, J. J. Pure Appl. Chem. 2002, 74, 1317-1325.
8. Li, H.; Blériot, Y.; Chantereau, C.; Mallet, J.; Sollogoub, M.; Zhang, Y.; Rodríguez-García, E.; Vogel, P.; Jiménez- Barbero, J.; Sinay, P. Org. Biomol. Chem. 2004, 2, 1492-1499.
9. Lee, S. J.; Beak, P. J. Am. Chem. Soc. 2006, 128, 2178-2179.
10. (a) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137-165.
11. (b) Denmark, S. E.; Cottell, J. J. Nitronates. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; John Wiley & Sons: New Jersey, 2003; Chapter 2.
12. (c) Denmark, S. E.; Seierstad, M. J. Org. Chem. 1999, 64, 1610-1619.
13. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 319-322.
14. (a) Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682-4698.
15. (b) Heemstra, J. R., Jr.; Denmark, S. E. J. Am. Chem. Soc. 2006, 128, 1038-1039.
16. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812-2820.
17. Ryu, I.; Yamamoto, H.; Sonoda, N.; Murai, S. Organometallics 1996, 15, 5459-5461.
18. 1H NMR analysis.
19. For spectroscopic data for the chloride adduct, see Supporting Information.
20. (a) Patrocínio, A. F.; Mora, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
21. (b) Page, P. C. B.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195.
22. (c) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660.
23. Peterson, D. J. J. Org. Chem. 1968, 33, 780-784.
24. Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
25. The formation of a lactam (amide) from an acylsilane and a hydroxylamine appears to be unprecedented. However, the analogy to the recently reported peptide ligation of hydroxylamines with α-keto acids is noteworthy. Bode, J. W.; Fox. R. M.; Baucom, K. D. Angew. Chem., Int. Ed. 2006, 45. 1248-1252.
26. Brook, A. G.; Duff, J. M. J. Am. Chem. Soc. 1967, 89, 454-455.
27. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1345-1353.