Highly functionalized, enantiomerically pure furo[x,y-c]pyrans via alkylidenecarbenes derived from sugar templates: synthesis and mechanism study via computational chemistry

Tetrahedron

Volumn 65, Issue 45, 2009, Pages 9378-9394

  Nguyen Van Nhien, Albert ^a   Cordonnier, Romaric ^a   Le Bas, Marie Delphine ^a   Delacroix, Sébastien ^a   Soriano, Elena ^b   Marco Contelles, José ^b   Postel, Denis ^a  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLIDENECARBENE; CARBENOID; CARBON; FURO[X,Y C]PYRAN DERIVATIVE; GALACTOSE; GLUCOSE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENANTIOMER; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 70349779339     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.080     Document Type: Article

References (62)

1. For reviews:
2. Stang P.J. Chem. Rev. 78 (1978) 383
3. Stang P.J. Angew. Chem., Int. Ed. Engl. 31 (1992) 274
4. Kirmse W. Angew. Chem., Int. Ed. 36 (1997) 1164
5. Knorr R. Chem. Rev. 104 (2004) 3795
6. Cunico R.F. J. Organomet. Chem. 105 (1976) C29-C31
7. Stang P.J., and Christensen S.B. J. Org. Chem. 46 (1981) 823
8. Stang P.J., and Fox D.P. J. Org. Chem. 42 (1977) 1667
9. Gilbert J.C., and Giamalva D.H. J. Org. Chem. 48 (1983) 5251
10. Ochiai M., Takaoka Y., and Nagao Y. J. Am. Chem. Soc. 110 (1988) 6565
11. Kunishima M., Hioki K., Tani S., and Kato A. Tetrahedron Lett. 35 (1994) 7253
12. Kim S., and Cho C.M. Tetrahedron Lett. 36 (1995) 4845
13. Czernecki S., and Valéry J.-M. J. Carbohydr. Chem. 5 (1986) 235
14. Pérez-Pérez M.J., and Camarasa M.J. J. Chem. Soc., Chem. Commun. (1992) 1403
15. Pérez-Pérez M.J., and Camarasa M.J. Tetrahedron 50 (1994) 7269
16. For some useful transformations of alkylidenecarbenes in sugar templates, see:
17. Tronchet J., González A., Zumwald J.B., and Perret F. Helv. Chim. Acta 57 (1974) 1505
18. Hauske J.R., Guadliana M., and Desai K. J. Org. Chem. 47 (1982) 5019
19. Ohira S., Sawamoto T., and Yamato M. Tetrahedron Lett. 36 (1995) 1537
20. Niizuma S., Shuto S., and Matsuda A. Tetrahedron 53 (1997) 13621
21. Wardrop D.J., Zhang W., and Frtz J. Org. Lett. 4 (2002) 489
22. Nguyen Van Nhien A., León R., Postel D., Carreiras M.C., García A.G., and Marco-Contelles J. J. Carbohydr. Chem. 24 (2005) 369
23. Examples of 1,6-C-H insertions on alkylidenecarbenes are rare:
24. Feldman K.S., and Perkins A.L. Tetrahedron Lett. 42 (2001) 6031
25. Gilbert J.C., and Blackburn B.K. Tetrahedron Lett. 31 (1990) 4727
26. Brown R.F.C., Eastwood F.W., Harrington K.J., and McMullen G.L. Aust. J. Chem. 27 (1974) 2393
27. Wittenberger S.J., and Donner B.G. J. Org. Chem. 58 (1993) 4139
28. For a review on the synthesis of 5-substituted 1H-tetrazoles, see:. Herr R.J. Bioorg. Med. Chem. 10 (2002) 3379
29. For the synthesis of related pyrano-anellated pyranosides, see:. Thiele G., Feist H., and Peseke K. J. Carbohydr. Chem. 24 (2005) 209
30. Marcelo F., Jiménez-Barbero J., Marrot J., Rauter A.P., Sinaÿ P., and Blériot Y. Chem.-Eur. J. 14 (2008) 10066
31. Ethève-Quelquejeu M., Xie J., and Valéry J.-M. Synlett (2004) 1089 and references cited therein
32. Qin H., and Grindley T.B. J. Carbohydr. Res. 15 (1996) 95
33. Rauter A.P., Oiliveira O., Canda T., Leroi E., Ferreira H., Ferreira M.J., and Ascenso J.A. J. Carbohydr. Chem. 21 (2002) 257
34. Français A., Urban D., and Beau J.-M. Angew. Chem., Int. Ed. 46 (2007) 8662
35. Dong L., Roosenberg II J.M., and Miller M.J. J. Am. Chem. Soc. 124 (2002) 15001
36. Lecourt T., Herault A., Pearce A.J., Sollogoub M., and Sïnaÿ P. Chem.-Eur. J. 10 (2004) 2960
37. Fürstner A., and Weidmann H. J. Org. Chem. 54 (1989) 2307
38. Deninno M.P., Etienne J.B., and Duplantier K.C. Tetrahedron Lett. 36 (1995) 669
39. Kenichi S., Tetsutaro I., Yukio Y., Nobuya K., Hironobu H., and Juji Y. Chem. Lett. 10 (1988) 1699
40. Attolino E., Cumpstey I., and Fairbanks A.J. Carbohydr. Res. 341 (2006) 1609
41. Tanaka N., Ogawa I., Yoshigase S., and Nokami J. Carbohydr. Res. 343 (2008) 2675
42. For some examples, see:
43. Jeziorek D., and Zurawski B. Int. J. Quantum Chem. 16 (1979) 277
44. Krishnan R., and Pople J.A. Int. J. Quantum Chem. Symp. 14 (1980) 91
45. Gordon M.S., and Gano D.R. J. Am. Chem. Soc. 106 (1984) 5421
46. Ramalingam M., Ramasami K., Venuvanalingam P., and Sethuraman V. THEOCHEM 755 (2005) 169
47. Ramalingam M., Ramasami K., and Venuvanalingam P. Chem. Phys. Lett. 430 (2006) 414
48. Fang R., Geng Z.Y., Wang Y.C., Zhao C.Y., Yang L.Z., and Zhang X.H. Chem. Phys. Lett. 414 (2005) 174
49. Yao K., Geng Z.-Y., Wang Y.-C., and Jia B.-L. THEOCHEM 821 (2007) 106
50. Takahashi O., Yamasaki K., Kohno Y., Ohtaki R., Ueda K., Suezawa H., Umezawad Y., and Nishio M. Carbohydr. Res. 342 (2007) 1202
51. For the importance of the CH/O hydrogen bond in chemistry and biochemistry, see. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), Oxford University Press, Oxford
52. Gilbert J.C., Giamalva D.H., and Baze M.E. J. Org. Chem. 50 (1985) 2557
53. A question of mechanistic relevance is the ground state multiplicity of these species. The computed mechanism for the insertion process in the triplet state (stepwise) diverges from that in the singlet state (concerted pathway). See Supplementary data for details.
54. Taber D.F., Meagley R.P., and Doren D.J. J. Org. Chem. 61 (1996) 5723
55. Karpf M., Huguet J., and Dreiding A.S. Helv. Chim. Acta 65 (1982) 13
56. Koller M., Karpf M., and Dreiding A.S. Helv. Chim. Acta 66 (1983) 2760
57. Gaussian 03 (2004), Gaussian, Wallingford, CT (see Supplementary data)
58. Becke A.D. J. Chem. Phys. 98 (1993) 5648
59. Lee W., Yang R.G., and Parr R.G. Phys. Rev. B 37 (1988) 785
60. Glendening E. D.; Reed A. E.; Carpenter J. E.; Weinhold F., NBO Version 3.1. For original literature, see:
61. Reed A.E., and Weinhold F. J. Chem. Phys. 78 (1983) 4066
62. Reed A.E., Curtiss L.A., and Weinhold F. Chem. Rev. 88 (1988) 899