Substrate-controlled stereodifferentiation of tandem [4 + 2]/[3 + 2] cycloadditions by a vicinal carbohydrate-based template

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1880-1882

  Avalos, Martin ^a   Babiano, Reyes ^a   Cintas, Pedro ^a   Higes, Francisco J ^a   Jiménez, José L ^a   Palacios, Juan C ^a   Silva, Maria A ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000998774     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951728e     Document Type: Article

References (36)

1. For reviews on tandem and domino-type reactions: (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (b) Ho, T.-L. Polarity Control for Synthesis; Wiley: New York, 1991. (c) Ziegler, F. E. In Comprehensive Organic Synthesis; Paquete, L. A., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 7.3. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
2. For reviews on tandem and domino-type reactions: (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (b) Ho, T.-L. Polarity Control for Synthesis; Wiley: New York, 1991. (c) Ziegler, F. E. In Comprehensive Organic Synthesis; Paquete, L. A., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 7.3. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
3. For reviews on tandem and domino-type reactions: (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (b) Ho, T.-L. Polarity Control for Synthesis; Wiley: New York, 1991. (c) Ziegler, F. E. In Comprehensive Organic Synthesis; Paquete, L. A., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 7.3. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
4. For reviews on tandem and domino-type reactions: (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. (b) Ho, T.-L. Polarity Control for Synthesis; Wiley: New York, 1991. (c) Ziegler, F. E. In Comprehensive Organic Synthesis; Paquete, L. A., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 7.3. (d) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
5. (a) Denmark, S. E.; Dappen, M. S.; Cramer, C. J. J. Am. Chem. Soc. 1986, 108, 1306.
6. (b) Denmark, S. E.; Cramer, C. J.; Sternberg, J. A. Helv. Chim. Acta 1986, 69. 1971.
7. (c) Denmark, S. E.; Moon, Y.-C.; Cramer, C. J.; Dappen, M. S.; Senanayake, C. B. W. Tetrahedron 1990, 46, 7373.
8. (d) Denmark, S. E.; Moon, Y.-C.; Senanayake, C. B. W. J. Am. Chem. Soc. 1990, 112, 311.
9. (e) Denmark, S. E.; Senanayake, C. B. W.; Ho, G.-D. Tetrahedron 1990, 46, 4857.
10. (f) Denmark, S. E.; Senanayake, C. B. W. J. Org. Chem. 1993, 58, 1853.
11. (g) Denmark, S. E.; Schnute, M. E.; Senanayake, C. B. W. J. Org. Chem. 1993, 58, 1859.
12. (h) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1993, 58, 3857.
13. (i) Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1994, 59, 5672.
14. (j) Denmark, S. E.; Schnute, M. E.; Thorarensen, A.; Middleton, D. S.; Stolle, A. Pure Appl. Chem. 1994, 66, 2041.
15. (k) Denmark, S. E.; Schnute, M. E.; Marcin, L. R.; Thorarensen, A. J. Org. Chem. 1995, 60, 3205.
16. (l) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1995, 60, 3221.
17. (m) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Org. Chem. 1995, 60, 3574.
18. Papchikhin, A.; Agback, P.; Plavec, J.; Chattopadhyaya, J. J. Org. Chem. 1993, 58, 2874.
19. Wade, P. A.; Giuliano, R. M. The Role of the Nitro Group in Carbohydrate Chemistry. In Nitro Compounds. Recent Advances in Synthesis and Chemistry; Feuer, H.; Nielsen, A. T., Eds.; VCH Publishers: New York, 1990: p 137.
20. Denmark has classified [4 + 2]/[3 + 2] cycloadditions into three subclasses: the fused, spiro, and bridged modes. In the fused mode the tether is linked to the nitroalkene β-carbon atom. See: Denmark, S. E.; Stolle, A.; Dixon, J. A.; Guagnano, V. J. Am. Chem. Soc. 1995, 117, 2100.
21. Sowden, J. C.; Strobach, D. R. J. Am. Chem. Soc. 1960, 82, 954.
22. See ref 3: Reactions were more stereoselective in ethanol than in dichloromethane. In the former only one nitronate and its cyctoadduct were detected. The "ethanol effect" has been also observed in [4 + 2] cycloadditions of α-chloronitroso compounds: (a) Labaziewicz, H.; Riddell, F. G. J. Chem. Soc., Perkin Trans. 1 1979, 2926. (b) Felber, H.; Kresze, G.; Prewo, R., Vasella, A. Helv. Chim. Acta 1986, 69, 1137.
23. See ref 3: Reactions were more stereoselective in ethanol than in dichloromethane. In the former only one nitronate and its cyctoadduct were detected. The "ethanol effect" has been also observed in [4 + 2] cycloadditions of α-chloronitroso compounds: (a) Labaziewicz, H.; Riddell, F. G. J. Chem. Soc., Perkin Trans. 1 1979, 2926. (b) Felber, H.; Kresze, G.; Prewo, R., Vasella, A. Helv. Chim. Acta 1986, 69, 1137.
24. The authors have deposited atomic coordinates for compound 2 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
25. Bond, D.; Schleyer, P. v. R. J. Org. Chem. 1990, 55, 1003 and references therein.
26. Apeloig, Y.; Matzner, E. J. Am. Chem. Soc. 1995, 117, 5375.
27. Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C.; Silva, M. A. Manuscript in preparation.
28. Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127.
29. Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663.
30. The inherent asymmetric environment provided by the carbohydrate chiron must affect the overlap with the approaching dienophile. Semiempirical calculations and an ab-initio study on a reduced model are in progress in search of transition states.
31. Japanese authors have shown the efficiency of the substrate stereocontrol exerted by a bis-silylated threo-diol structure onto the π-faces of the alkene: (a) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (b) Saito, S.; Ishikawa, T.; Kishimoto, N.; Kohara, T.; Moriwake, T. Synlett 1994, 282.
32. Japanese authors have shown the efficiency of the substrate stereocontrol exerted by a bis-silylated threo-diol structure onto the π-faces of the alkene: (a) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (b) Saito, S.; Ishikawa, T.; Kishimoto, N.; Kohara, T.; Moriwake, T. Synlett 1994, 282.
33. In some cases, plates of 3 were grown under vacuum, but any attempt to solve the structure failed because of the absence of reflections at room temperature, thus confirming its amorphous character.
34. Chiral isoxazolines have been previously obtained through asymmetric thermal cycloadditions with mtrile oxides. Kim, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293.
35. For reviews on branched and higher carbon sugars: (a) Yoshimura, J. Adv. Carbohydr. Chem. Biochem. 1984, 42, 69. (b) Zamojski, A.; Jarosz, S. Pol. J. Chem. 1992, 66, 525 and references therein.
36. For reviews on branched and higher carbon sugars: (a) Yoshimura, J. Adv. Carbohydr. Chem. Biochem. 1984, 42, 69. (b) Zamojski, A.; Jarosz, S. Pol. J. Chem. 1992, 66, 525 and references therein.