Tandem [4 + 2]/[3 + 2] Cycloadditions with Nitroethylene

Journal of Organic Chemistry

Volumn 63, Issue 9, 1998, Pages 3045-3050

  Denmark, Scott E ^a   Hurd, Alexander R ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000048441     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972280f     Document Type: Article

References (40)

1. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
2. (a) Denmark, S. E.; Senanayake, C. B. W.; Ho, G.-D. Tetrahedron 1990, 46, 4857.
3. (b) Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1991, 56, 6738.
4. Denmark, S. E.; Schnute, M. E.; Senanayake, C. B. W. J. Org. Chem. 1993, 58, 1859.
5. Denmark, S. E.; Schnute, M. E.; Marcin, L. R.; Thorarensen, A. J. Org. Chem. 1995, 60, 3205.
6. (e) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1996, 61, 6727.
7. Denmark, S. E.; Kesler, B. S.; Moon, Y.-C. J. Org. Chem. 1992, 57, 4912.
8. (a) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1993, 58, 3857.
9. (b) Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1994, 69, 4576.
10. (c) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1995, 60, 3221.
11. Denmark, S. E.; Middleton, D. S J. Org. Chem. 1998, 63, 1604.
12. Buckley, G. D.; Scaife, C. W. J. Chem. Soc. 1947, 1471.
13. Chlenov, I. E.; Morozova, N. S.; Khudak, V. I.; Tartakovskii, V. A. Izv. Akad. Nauk. SSSR, Ser. Chem. 1970, 2641 (English translation, Bull. Acad. Sci., SSSR 1970, 2492).
14. Chlenov, I. E.; Morozova, N. S.; Khudak, V. I.; Tartakovskii, V. A. Izv. Akad. Nauk. SSSR, Ser. Chem. 1970, 2641 (English translation, Bull. Acad. Sci., SSSR 1970, 2492).
15. Ranganathan, D.; Rao, C. B.; Ranganathan, S.; Mehrotra, A. K.; Iyengar, R. J. Org. Chem. 1980, 45, 1185-1189 and references therein.
16. Tucker, J. A.; Clayton, T. L.; Mordas, D. M. J. Org. Chem. 1997, 62, 4370.
17. Nitroethylene is easily prepared by the dehydration of nitroethanol with phthallic anhydride (see ref 6), and despite reports concerning its instability, it can be stored as a neat oil at -20°C for several months without loss in purity.
18. Methylaluminum bis(2,6-diphenylphenoxide). Nonoshita, X.; Banno, H.; Maruoka, K.; Yamomoto, H. J. Am. Chem. Soc. 1990, 112, 316.
19. Trimethylaluminum also promoted the cycloaddition but was not diastereoselective.
20. 2NH/ MeOH or KOH/MeOH) excess nitroethylene would undergo [3 + 2] cycloaddition prior to or at least competitive with its destruction.
21. Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 60, 5672.
22. In reactions with a nitronate system which is highly facially selective, dimethyl fumarate was poorly endo/exo selective (1/1). Denmark, S. E.; Herbert B.; Seierstad, M. J., unpublished results.
23. The probable structures of the other four diastereomers are shown below. All nitroso acetals have the same relative configuration of the chiral auxiliary (OG*).
24. Methyl acrylate has been shown to react with exo selectivity. See ref 15.
25. The enantiomeric excess was determined by chiral-stationary- phase, supercritical-fluid chromatography (SFC) (Chiralcel OD, 150 bar, 5% MeOH, 2 mL/min, 220 nm).
26. The enantiomeric excess was determined by chiral-stationary- phase, supercritical-fluid chromatography (SFC) (Chiralcel AD, 150 bar, 20% MeOH, 3 mL/min, 220 nm). The mother liquor contained a mixture of (+)-10 and an unidentified hydroxy lactam, indicating that the other nitroso acetal diastereomer present in (+)-6c was of a different enantiomeric family.
27. Hydroxy lactam 12 was isolated in 10% yield and is derived from nitroso acetal 7c' which is the endo addition product of methyl acrylate to nitronate 2c.
28. 23 = +49.3° (EtOH, c = 0.50). (a) Danilova, A.; Utkin, L.; Massagetov, P. J. Gen. Chem. USSR. 1955, 25, 797.
29. (b) Ito, H.; Ikeuchi, Y.; Taguchi, T.; Hanazawa, Y.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 5469.
30. 23 = -20.0° (EtOH, c = 0.25). (a) Yamada, K.; Tatematsu, H.; Unno, R.; Hirata, Y.; Hirono, I. Tetrahedron Lett. 1978, 4543.
31. (b) Mulzer, J.; Shanyoor, M. Tetrahedron Lett. 1993, 34, 6545.
32. Pecunioso, A.; Menicagli, R. J. Org. Chem. 1988, 53, 45.
33. A kinetic anomeric effect has been used to rationalize stereo- selective [3 + 2] cycloadditions of nitrones (Vasella, A. Helv. Chim. Acta 1977, 60, 1273, Petrizilka, M.; Felix, D.; Eschenmoser, A. Helv. Chim. Acta 1973, 56, 2950) and nitronates (Denmark, S. E.; Dappen, M. S.; Cramer, C. J. J. Am. Chem. Soc. 1986, 108, 1306. Denmark, S. E.; Cramer, C. J.; Sternberg, J. A. Helv. Chim. Acta 1986, 69, 1971).
34. A kinetic anomeric effect has been used to rationalize stereo- selective [3 + 2] cycloadditions of nitrones (Vasella, A. Helv. Chim. Acta 1977, 60, 1273, Petrizilka, M.; Felix, D.; Eschenmoser, A. Helv. Chim. Acta 1973, 56, 2950) and nitronates (Denmark, S. E.; Dappen, M. S.; Cramer, C. J. J. Am. Chem. Soc. 1986, 108, 1306. Denmark, S. E.; Cramer, C. J.; Sternberg, J. A. Helv. Chim. Acta 1986, 69, 1971).
35. A kinetic anomeric effect has been used to rationalize stereo- selective [3 + 2] cycloadditions of nitrones (Vasella, A. Helv. Chim. Acta 1977, 60, 1273, Petrizilka, M.; Felix, D.; Eschenmoser, A. Helv. Chim. Acta 1973, 56, 2950) and nitronates (Denmark, S. E.; Dappen, M. S.; Cramer, C. J. J. Am. Chem. Soc. 1986, 108, 1306. Denmark, S. E.; Cramer, C. J.; Sternberg, J. A. Helv. Chim. Acta 1986, 69, 1971).
36. A kinetic anomeric effect has been used to rationalize stereo- selective [3 + 2] cycloadditions of nitrones (Vasella, A. Helv. Chim. Acta 1977, 60, 1273, Petrizilka, M.; Felix, D.; Eschenmoser, A. Helv. Chim. Acta 1973, 56, 2950) and nitronates (Denmark, S. E.; Dappen, M. S.; Cramer, C. J. J. Am. Chem. Soc. 1986, 108, 1306. Denmark, S. E.; Cramer, C. J.; Sternberg, J. A. Helv. Chim. Acta 1986, 69, 1971).
37. The ground state conformation of the minor diastereomers in all tandem cycloadditions has an equatorially disposed C(6) alkoxy substituent, as determined by NMR analysis.
38. (a) Denmark, S. E.; Stolle, A.; Dixon, J. A.; Guagnano, V. J. Am. Chem. Soc. 1995, 117, 2100.
39. (b) Denmark, S. E.; Guagnano, V.; Dixon, J. A.; Stolle, A. J. Org. Chem. 1997, 62, 4610.
40. (c) Denmark, S. E.; Dixon, J. A. J. Org. Chem. 1997, 62, 7086.