Transition metal-catalyzed syntheses of 'rod-like' thioglycoside dimers

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1155-1158

  Gan, Zhonghong ^a   Roy, René ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; DIMER; METAL; PALLADIUM; THIOGLYCOSIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; REACTION ANALYSIS; SYNTHESIS;

EID: 0034685260     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02285-6     Document Type: Article

References (21)

1. Stang, P. J.; Diederich, F. Modern Acetylene Chemistry; Wiley-VCH: Weinheim, Germany, 1995.
2. For reviews, see: (a) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 551-561. (b) Brandsma, L.; Vasilevsky, S. F.; VerKruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1998; pp. 179-225.
3. For reviews, see: (a) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 551-561. (b) Brandsma, L.; Vasilevsky, S. F.; VerKruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1998; pp. 179-225.
4. For reviews, see: (a) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 521-549. (b) Brandsma, L.; Vasilevsky, S. F.; VerKruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1998; pp. 67-83. (c) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp. 203-229.
5. For reviews, see: (a) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 521-549. (b) Brandsma, L.; Vasilevsky, S. F.; VerKruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1998; pp. 67-83. (c) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp. 203-229.
6. For reviews, see: (a) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 521-549. (b) Brandsma, L.; Vasilevsky, S. F.; VerKruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1998; pp. 67-83. (c) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp. 203-229.
7. For examples of Glaser reaction and Sonogahira reaction using organosulfur compounds, see: (a) Müller, T. J. J. Tetrahedron Lett. 1999, 40, 6563-6566. (b) Fossatelli, M.; Van der Kerk, A. C. T. H. M.; Vasilevsky, S. F.; Brandsma, L. Tetrahedron Lett. 1992, 33, 4229-4232. (c) Neen, T. X.; Whitesides, G. M. J. Org. Chem. 1988, 53, 2489-2496. (d) Fritzsche, V.; Hunig, S. Tetrahedron Lett. 1972, 4831-4834.
8. For examples of Glaser reaction and Sonogahira reaction using organosulfur compounds, see: (a) Müller, T. J. J. Tetrahedron Lett. 1999, 40, 6563-6566. (b) Fossatelli, M.; Van der Kerk, A. C. T. H. M.; Vasilevsky, S. F.; Brandsma, L. Tetrahedron Lett. 1992, 33, 4229-4232. (c) Neen, T. X.; Whitesides, G. M. J. Org. Chem. 1988, 53, 2489-2496. (d) Fritzsche, V.; Hunig, S. Tetrahedron Lett. 1972, 4831-4834.
9. For examples of Glaser reaction and Sonogahira reaction using organosulfur compounds, see: (a) Müller, T. J. J. Tetrahedron Lett. 1999, 40, 6563-6566. (b) Fossatelli, M.; Van der Kerk, A. C. T. H. M.; Vasilevsky, S. F.; Brandsma, L. Tetrahedron Lett. 1992, 33, 4229-4232. (c) Neen, T. X.; Whitesides, G. M. J. Org. Chem. 1988, 53, 2489-2496. (d) Fritzsche, V.; Hunig, S. Tetrahedron Lett. 1972, 4831-4834.
10. For examples of Glaser reaction and Sonogahira reaction using organosulfur compounds, see: (a) Müller, T. J. J. Tetrahedron Lett. 1999, 40, 6563-6566. (b) Fossatelli, M.; Van der Kerk, A. C. T. H. M.; Vasilevsky, S. F.; Brandsma, L. Tetrahedron Lett. 1992, 33, 4229-4232. (c) Neen, T. X.; Whitesides, G. M. J. Org. Chem. 1988, 53, 2489-2496. (d) Fritzsche, V.; Hunig, S. Tetrahedron Lett. 1972, 4831-4834.
11. Vasella, A. Pure Appl. Chem. 1998, 70, 425-430.
12. Witczak, Z. J.; Chhabra, R.; Chen. H.; Xie, X.-Q. Carbohydr. Res. 1997, 301, 167-175.
13. (b) Shafizadeh, F.; Furneaux, R. H.; Stevenson, T. T. Carbohydr. Res. 1979, 71, 169-191.
14. Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863-1933.
15. (a) Horton, D. Methods Carbohydr. Chem. 1963, 2, 433-437.
16. (b) García-López, J. J.; Hernández-Mateo, F.; Isac-García, J.; Kim, J. M.; Roy, R.; Santoyo-González, F.; Vargas-Berenguel, A. J. Org. Chem. 1999, 68, 522-531.
17. Hay, A. S. J. Org. Chem. 1962, 27, 3320-3321.
18. Roy, R.; Das, S. K.; Dominique, R.; Trono, M. C.; Hernández-Mateo, F.; Santoyo-González, F. Pure Appl. Chem. 1999, 71, 565-572.
19. 2C).
20. Austin, W. B.; Bilow, N.; Kelleghan, W. J.; Lau, K. S. Y. J. Org. Chem. 1981, 46, 2280-2286.
21. Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551-8553.