Palladium-catalysed cyclisation of chiral carbohydrate-derived geminal diacetates

Tetrahedron

Volumn 55, Issue 11, 1999, Pages 3467-3478

  Holzapfel, Cedric W ^a   Marais, Lizel ^a   Toerien, Francois ^a  

^a UNIVERSITY OF JOHANNESBURG   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID DERIVATIVE; CARBOHYDRATE; PALLADIUM;

ARTICLE; CHIRALITY; CYCLIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0033105341     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01155-7     Document Type: Article

References (36)

1. (a) Oppolzer, W. Angew. Chem. Int. Ed. Engl. 1989, 28, 38.
2. (b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I.; Paquette, L.A. Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 1.2.
3. (c) Oppolzer, W. Pure Appl. Chem. 1990, 62, 1941.
4. Holzapfel, C.W.; Marais, L. Tetrahedron Lett. 1998, 39, 2179.
5. (a) Toerien, F. Ph.D. Thesis, Rand Afrikaans University, 1995.
6. (b) Marais, L. Ph.D. Thesis, Rand Afrikaans University, 1998.
7. (a) Faulkner, J.D. J. Nat. Prod. Rep. 1992, 9, 323.
8. (b) Robinson, J.A. Fortschr. Chem. Org. Naturst. 1991, 58, 1.
9. (c) Corey, E.J.; Cheng, X.-M. The Logic of Chemical Synthesis, Wiley: New York, 1989.
10. (d) Boivin, T.L. Tetrahedron 1987, 43, 3309 and cited references.
11. Balog, A.; Yu, M.S.; Curran, D.P.; Yu, G.; Carcanague, D.R.; Shue, Y.-K. Synth. Commun. 1996, 26, 935.
12. Gonzalez, F.; Lesage, S.; Perlin, A.S. Carbohydr. Res. 1975, 42, 267.
13. Ferner, R.J., Prasad, N. J. Chem. Soc. (C) 1969, 570.
14. Holzapfel, C.W.; Engelbrecht, G.J.; Marais, L.; Toerien, F. Tetrahedron 1997, 53, 3957.
15. Deka, N.; Kalita, D.J.; Borah, R.; Sarma, J.C. J. Org. Chem. 1997, 62, 1563.
16. Brown, A.C.; Carpino, L.A. J. Org. Chem. 1988, 50, 1749.
17. (a) Oppolzer, W.; Bedoya-Zurita, M.; Switzer, C.Y. Tetrahedron Lett. 1988, 29, 6433.
18. (b) Gómez-Bengoa, E.; Cuerva, J.M.; Echavarren, A.M.; Martorell, G. Angew. Chem. Int. Ed. Engl. 1997, 36, 767.
19. Oppolzer, W.; Keller, T.H.; Kuo, D.L.; Pachinger, W. Tetrahedron Lett. 1990, 31, 1265.
20. (a) Tomioka, K. Synthesis 1990, 541.
21. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
22. (c) Wills, M. Chem. Soc. Rev. 1995, 177.
23. Oppolzer, W.; Kuo, D.L.; Hutzinger, M.W.; Léger, R.; Durand, J.-O.; Leslie, C. Tetrahedron Lett. 1997, 38, 6213.
24. Brown, J.M. Angew. Chem. Int. Ed. Engl. 1987, 26, 190 and cited references.
25. Oppolzer, W.; Schröder, F. Tetrahedron Lett. 1994, 35, 7939.
26. Oppolzer, W.; Ruiz-Montes, J. Helv. Chim. Acta 1993, 76, 1266.
27. (a) Trost, B.M. Angew. Chem. Int. Ed. Engl. 1995, 34, 259.
28. (b) Trost, B.M. Science 1991, 254, 1471.
29. (a) Trost, B.M. Acc. Chem. Res. 1990, 23, 34.
30. (b) Trost, B.M. Janssen Chim. Acta 1991, 9, 3.
31. (c) Trost, B.M.; Krische, M.J. Synlett 1998, 1.
32. (d) Trost, B.M.; Romero, D.L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268.
33. Jiang, H.; Ma, S.; Zhu, G.; Lu, X. Tetrahedron 1996, 52, 10945 and cited references.
34. Nilsson, Y.I.M.; Gatti, R.G.P.; Andersson, P.G.; Bäckvall, J.E. Tetrahedron 1996, 52, 7511.
35. (a) Hosokawa, T.; Murahashi, S.-I. Acc. Chem. Res. 1990, 23, 49.
36. (b) Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027.