Intramolecular [4 + 2] cycloaddition of nitroalkenes for construction of vicinal quaternary stereocenters

Organic Letters

Volumn 7, Issue 25, 2005, Pages 5617-5620

  Denmark, Scott E ^a   Baiazitov, Ramil Y ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; NITRO DERIVATIVE;

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

ALKENES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 29444435549     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052316n     Document Type: Article

References (20)

1. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
2. Peterson, E. A.; Overman, L. E. Proc. Nat. Acad. Sci. 2004, 101, 11943-11948.
3. Von Nussbaum, F.; Hanke, R.; Fahrig, T.; Benet-Buchholz, J. E. J. Org. Chem. 2004, 2783-2790.
4. (b) Nicolaou, K. C.; Vassilikogiannakis, G.; Magerlein, W.; Kranich, R. Chem. Eur. J. 2001, 7, 5359-5371.
5. (c) Heathcock, C. H.; Hansen, M. M.; Ruggeri, R. B.; Kath, J. C. J. Org. Chem. 1992, 57, 2544-2553.
6. (a) Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1994, 59, 4576-4595.
7. (b) Denmark, S. E.; Gomez, L. J. Org. Chem. 2003, 68, 8015-8024.
8. See also: (c) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1997, 62, 1675-1686.
9. Denmark, S. E.; Baiazitov, R. Y. J. Org. Chem. in press (JO052001L).
10. (a) Tamura, R.; Sato, M.; Oda, D. J. Org. Chem. 1986, 51, 4368-4375.
11. (b) Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1995, 60, 1013-1019.
12. (a) Jubert, C.; Knochel, P. J. Org. Chem. 1992, 57, 5431-5438.
13. (b) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1993, 58, 3850-3856.
14. Roulland, E.; Monneret, C.; Florent, J.-C. J. Org. Chem. 2002, 67, 4399-4406.
15. Seebach, D.; Henning, R.; Mukhopadhyay, T. Chem. Ber. 1982, 115, 1705-1720.
16. Reich, H. J.; Wollowitz, S. Org. React. 1993, 44, 1-296.
17. Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1689-1697.
18. (a) Reich, H. J.; Renga, J. M.; Reich, I. L. J. Am. Chem. Soc. 1975, 97, 5434.
19. (b) Smith, A. B., III; Empfield, J. R.; Rivero, R. A.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 4037-4038.
20. The crystallographic coordinates of 2a and 2b have been deposited with the Cambridge Crystallographic Data Centre, deposition nos. CCDC 282324 and 282325, respectively. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax (+44) 1223-336-033; email deposit@ccdc.cam.ac.uk).