Stereocontrolled palladium(0) catalysed cyclisation and cyclisation/carbonylation of pseudoglycal derivatives

Tetrahedron

Volumn 53, Issue 11, 1997, Pages 3957-3974

  Holzapfel, Cedric W ^a   Engelbrecht, Gerhard J ^a   Marais, Lizel ^a   Toerien, Francois ^a  

^a UNIVERSITY OF JOHANNESBURG   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; PALLADIUM; PYRANOSIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHROMATOGRAPHY; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0031575856     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00012-4     Document Type: Article

References (49)

1. 1. Ferrier, R.J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831 and cited references.
2. 2 . Fraser-Reid, B. Acc. Chem. Res. 1985, 18, 347-354.
3. 3 . Grové, J.J.C.; Holzapfel, C.W.; Williams, D.B.G. Tetrahedron Lett. 1996, 37, 1305-1308 and 5817-5820.
4. 4 . Holzapfel, C.W.; van der Merwe, T.L. Tetrahedron Lett. 1996, 37, 2303-2306 and 2307-2310.
5. 5. Pipelier, M.; Ermolenko, M.S.; Zampella, A.; Olesker, A.; Lukacs, G. Synlett 1996, 24-26 and cited references.
6. 6. For recent reviews: a) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365-393.
7. b) Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975-1015.
8. c) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289-9346.
9. d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J. Chem. Rev. 1996, 96, 635-662.
10. 7. Reviews: a) Oppolzer, W., in Comprehensive Organic Synthesis, Trost; B.M.; Fleming, I. Eds., Pergamon Press: Oxford, 1991; Vol.5, pp. 29-61.
11. b) Oppolzer, W. Pure Appl. Chem. 1990, 62, 1941-1948.
12. c) Oppolzer, W. Angew. Chem. Int. Ed. Engl. 1989, 28, 38-52.
13. 8. Preliminary results on this work: Engelbrecht, G.J.; Holzapfel, C.W. Tetrahedron Lett. 1991, 32, 2161-2164.
14. 9. For an improved synthetic protocol: Balog, A.; Yu, M.S.; Curran, D.P.; Yu, G.; Carcanague, D.R.; Shue, Y.-K. Synth. Commun. 1996, 26, 935-944.
15. 10. Ferrier, R.J.; Prasad, N. J. Chem. Soc. C 1969, 570-575.
16. 11. Baer, H.H.; Hanna, Z.S. Can. J. Chem. 1981, 59, 889-906.
17. 12. Acetic acid is the solvent of choice for these reactions, as indicated by the work of Oppolzer and other laboratories: a) Keese, R.; Guidetti-Grept, R.; Herzog, B. Tetrahedron Lett. 1992, 33, 1207-1210.
18. b) Terakado, M.; Murai, K.; Miyazawa, M.; Yamamoto, K. Tetrahedron 1994, 50, 5705-5718.
19. 13. Brakta, M.; Lhoste, P.; Sinou, D. J. Org. Chem. 1989, 54, 1890-1896.
20. 14. Deslongchamps, P. Pure Appl. Chem. 1993, 65, 1161-1178.
21. 15. Oppolzer, W.; Gaudin, J.-M. Helv. Chim. Acta 1987, 70, 1477-1481.
22. 16. Trost, B.M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1173-1192.
23. 17. a) Trost, B.M. Acc. Chem. Res. 1990, 23, 34-42.
24. b) Trost, B.M.; Romero, D.L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268-4278.
25. c) Trost, B.M.; Czeskis, B.A. Tetrahedron Lett. 1994, 35, 211-214.
26. d) Trost, B.M. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281 and cited references.
27. 18. Prepared by reduction of the corresponding isopropoxy pseudoglucal by the method of Grynkiewicz, G. Carbohydr. Res. 1984, 128, C9-C10.
28. 2 (0.1 mol equiv.) in acetic anhydride at 0 °C. The solution was quite dilute so as to prevent competing disaccharide formation.
29. 20. Nguefack, J.-F.; Bollit, V.; Sinou, D. Tetrahedron Lett. 1996, 37, 59-62.
30. 21. a) Marco-Contelles, J. Tetrahedron Lett. 1994, 35, 5059-5062.
31. b) Naz, N.; Al-Tel, T.H.; Voelter, W. Tetrahedron Lett. 1994, 35, 8581-8582.
32. c) Lindsell, W.E.; Preston, P.N.; Rettie, A.B. Carbohydr. Res. 1994, 254, 311-316.
33. 22. a) Oppolzer, W.; Keller, T.H.; Bedoya-Zurita, M.; Stone, C. Tetrahedron Lett. 1989, 30, 5883-5886.
34. b) Oppolzer, W.; Bienaymé, H.; Genevois-Borella, A. J. Am. Chem. Soc. 1991, 113, 9660-9661.
35. c) Oppolzer, W.; Xu, J.-Z.; Stone, C. Helv. Chim. Acta 1991, 74, 465-468.
36. 23. a) Takahashi, Y.; Tsujiyama, K.; Sakai, S.; Ishii, Y. Tetrahedron Lett. 1970, 1913-1916.
37. b) Bäckvall, J.-E.; Nordberg, R.E.; Björkman, E.E.; Moberg, C. J. Chem. Soc., Chem. Commun. 1980, 943-944.
38. c) Yamamoto, T.; Akimoto, M.; Saito, O.; Yamamoto, A. Organometallics 1986, 5, 1559-1567.
39. 24. a) Pérez-Pérez, M.J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1996, 6, 937-985.
40. b) Angerbauer, R.; Schmidt, R.R. Carbohydr. Res. 1981, 89, 193-201.
41. 25. Trost, B.M.; Gowland, F.W. J. Org. Chem. 1979, 44, 3448-3450 and cited references.
42. 26. Fischer, P., in Supplement E: The chemistry of ethers, crown ethers, hydroxyl groups and their sulphur analogues; Part 2; Patai, S. Ed.; John Wiley & Sons: Chichester, 1980; chap. 17, pp.761-820.
43. 27. An analogous anhydride species has been postulated: Catellani, M.; Chiusoli, G.P. Gazz. Chim. Ital. 1996, 126, 57-67.
44. 28. Abelman, M.M.; Oh, T.; Overman, L.E. J. Org. Chem. 1987, 52, 4130.
45. 29. Perrin, D.D.; Armarego, W.L.F. Purification of Laboratory Chemicals, 3rd edn.; Pergamon Press: Oxford, 1988.
46. 30. Heck, R.F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
47. 3: Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J.J.; Ibers, J.A. J. Organomet. Chem. 1974, 65, 253-266.
48. 32. Furniss, B.M.; Hannaford, A.J.; Smith, P.W.G.; Tatchell, A.R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman Scientific & Technical: New York, 1989; p.432.
49. 33. Colquhoun, H.M.; Thompson, D.J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds, Plenum Press: New York, 1991; pp. 46-49.