Reciprocal Donor Acceptor Selectivity (RDAS) and Paulsen's concept of "match" in saccharide coupling

European Journal of Organic Chemistry

Volumn , Issue 7, 2004, Pages 1387-1395

  Fraser Reid, Bert ^a   López, J Cristóbal ^b   Gómez, Ana M ^b   Uriel, Clara ^b  

^a Nat Prod/Glycotech Res Inst I   (United States)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Glycosides; Glycosylation; Regioselectivity

Indexed keywords

GLYCOSIDE; OLIGOSACCHARIDE;

CARBOHYDRATE SYNTHESIS; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; ENANTIOSELECTIVITY; GLYCOSYLATION; SHORT SURVEY; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 2942512558     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300689     Document Type: Short Survey

References (56)

1. H. Paulsen, Angew. Chem. Int. Ed. Engl. 1982, 21, 155-173.
2. H. Paulsen, in Selectivity a Goal for Synthetic Efficiency (Eds.: W. Bartmann, B. M. Trost), Verlag Chemie, Basel, 1984.
3. C. A. A. Van Boeckel, M. Petitou, Angew. Chem. Int. Ed. Engl. 1993, 32, 1671-1690.
4. [4a] O. J. Plante, E. R. Palmacci, P. H. Seeberger, Science 2001, 291, 1523-1527.
5. [4b] O. J. Plante, E. R. Palmacci, R. B. Andrade, P. H. Seeberger, J. Am. Chem. Soc. 2001, 123, 9545-9554.
6. P. Sears, C. H. Wong, Science 2001, 291. 2344-2350.
7. S. Nishimura, Baiosaiensu to Indasutori 2002, 60, 519.
8. D. K. Baeschlin, A. R. Chaperon, L. G. Green, M. G. Hahn, S. Ince, S. V. Ley, Chem. Eur. J. 2000, 6, 172-186.
9. Z. Zhang, I. R. Ollmann, X-S. Ye, R. Wischnat, T. Baasov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734-753.
10. A. Pictet, H. Vogel, Helv. Chim. Acta 1928, 11, 436-442.
11. [10a] H. S. Isbell, Ann. Rev. Biochem. 1940, 9, 65-92.
12. [10b] H. L. Frush, H. S. Isbell, J. Res. NBS 1941, 27, 413-425.
13. B. Capon, S. P. McManus, Neighboring Group Participation, Plenum, New York, 1976.
14. S. W. Winstein, R. E. Buckles, J. Am. Chem. Soc. 1942, 64, 2781-2786.
15. R. U. Lemieux, Adv. Carbohydr. Chem. 1954, 9, 1-57.
16. However for use of unprotected glycosyl donors, see: B. Lou, G. V. Reddy, H. Wang, S. Hanessian, in Preparative Carbohydrate Chemistry (Ed.: S. Hanessian), Marcel Dekker: New York, 1997, 389.
17. D. R. Mootoo, P. Konradsson, U. Udodong, B. Fraser-Reid, J. Am. Chem. Soc. 1988, 110, 5583-5584.
18. B. Fraser-Reid, Z. Wu, U. E. Udodong, H. Ottosson, J. Org. Chem. 1990, 55, 6068-6070.
19. H. Paulsen, A. Richter, V. Sinnwell, W. Stenzel, Carbohydr. Res. 1978, 64, 339-362.
20. B. Fraser-Reid, Z. Wu, C. W. Andrews, E. Skowronski, J. P. Bowen, J. Am. Chem. Soc. 1991, 113, 1434-1435.
21. [19a] Monosaccharides Their Chemistry and Their Roles in Natural Products (Eds.: P. M. Collins, R. J. Ferrier), John Wiley & Sons, Chichester, England, 1995.
22. [19b] Carbohydrate Chemistry (Ed.: G.-J. Boons), Blackie Academic & Professional, London, UK, chapter 5, 1998.
23. For two recent examples see: [20a] I. Cumpstey, T. D. Butters, R. J. Tennant-Eyles, A. J. Fairbanks, R. R. France, M. R. Wormald, Carbohydr. Res. 2003, 338, 1937-1949.
24. [20b] J. Lindberg, S. C. T. Svensson, P. Pahlsson, P. Konradsson, Tetrahedron 2002, 58, 5109-5117.
25. G.-J. Boons, R. Guersten, G. J. Holmes, J. Org. Chem. 1997, 62, 8145-8154.
26. M. Lahman, S. Oscarson, Can. J. Chem. 2002, 80, 889-893.
27. K. M. Koeller, C.-H. Wong, Chem. Rev. 2000, 100, 4465-4494.
28. L. Green, B. Hinzen, S. J. Ince, P. Langer, S. V. Ley, S. L. Warriner, Synlett 1998, 440-442.
29. G.-J. Boons, P. Grice, R. Leslie, S. V. Ley, L. L. Yeung, Tetrahedron Lett. 1993, 34, 8523-8526.
30. [26a] R. Roy, F. Andersson, Tetrahedron Lett. 1992, 33, 6053-6056.
31. [26b] G.-J. Boons, S. Isles, Tetrahedron Lett. 1994, 35, 3593-3596.
32. O. Kanie, Y. Ito, T. Ogawa, J. Am. Chem. Soc. 1994, 116, 12073-12074.
33. A. V. Demchenko, C. D. Meo, Tetrahedron Lett. 2002, 43, 8819-8822.
34. [29a] For excellent summaries of his work, see: A. Vasella, in Bioorganic Chemistry: Carbohydrates (Ed.: S. M. Hecht), Oxford University Press, New York, 1999, chapter 2.
35. [29b] A. Vasella, Pure Appl. Chem. 1993, 65, 731-752.
36. B. Bernet, A. Vasella, Helv. Chem. Acta 2000, 83, 995-1021.
37. G. Anilkumar, L. G. Nair, B. Fraser-Reid, Org. Lett. 2000, 2, 2587-2589.
38. H. M. Zuurmond, G. A. van der Marel, J. H. van Boom, Recl. Trav. Chim. Pays-Bas 1993, 112, 507-510.
39. B. Fraser-Reid, J. C. López, K. V. Radhakrishnan, M. Mach, U. Schlueter, A. M. Gómez, C. Uriel, Can. J. Chem. 2002, 124, 1075-1087.
40. C. J. J. Elie, C. E. Verduyn, D. M. Dreff, D. G. A. Brounts, G. A. van der Marel, J. H. van Boom, Tetrahedron 1990, 46, 8243-8254.
41. C. J. J. Elie, C. E. Verduyn, D. M. Dreff, D. G. A. Brounts, G. A. van der Marel, J. H. van Boom, J. Carbohydr. Chem. 1992, 11, 715-739.
42. G. Anilkumar, M. R. Gilbert, B. Fraser-Reid, Tetrahedron 2000, 56, 1993-1997.
43. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen (Ed.: A. J. Kirby), Springer-Verlag, New York, 1983.
44. In a typical proof of regioselectivity, the product was acylated and the down-shifted proton analyzed for its vicinal couplings.
45. B. Fraser-Reid, G. N. Anilkumar, L. G. Nair, K. V. Radhakrishnan, J. C. López, A. Gómez, C. Uriel, Aust. J. Chem. 2002, 55, 123-130.
46. B. Fraser-Reid, J. C. López, K. V. Radhakrishnan, M. V. Nandakumar, A. M. Gómez, C. Uriel, Chem. Commun. 2002, 2104-2105.
47. M. Mach, U. Schlueter, F. Mathew, B. Fraser-Reid, K. C. Hazen, Tetrahedron 2002, 58, 7345-7354.
48. J. C. López, A. M. Gómez, C. Uriel, B. Fraser-Reid, Tetrahedron Lett. 2003, 44, 1417-1420.
49. R. S. Brown, Acc. Chem. Res. 1997, 30, 131-137.
50. R. Rodebaugh, B. Fraser-Reid, J. Am. Chem. Soc. 1994, 116, 3155-3156.
51. G-J. Boons, T. Stauch, Synlett 1996, 906-908.
52. K. P. R. Kartha, P. Cura, M. Aloui, S. K. Readman, T. J. Rutherford, R. A. Field, Tetrahedron: Asymmetry 2000, 11, 581-593.
53. C. Uriel, A. M. Gómez, J. C. López, B. Fraser-Reid, unpublished results.
54. B. Fraser-Reid, S. Grimme, M. Piacenza, M. Mach, U. Schlueter, Chem. Eur. J. 2003, 9, 4687-4692.
55. B. G. Wilson, B. Fraser-Reid, J. Org. Chem. 1995, 60, 317-320.
56. Interestingly, the calculations [48] show that in the case of gluco derivatives there is no energy distinction between di- and trioxolenium ions as there is in their manno counterparts.