A diastereoselective unique route to cyclopropanes functionalized at all three ring carbon atoms from acyclic vinyl sulfone-modified carbohydrates

Journal of Organic Chemistry

Volumn 74, Issue 7, 2009, Pages 2710-2717

  Atta, Ananta Kumar ^a   Pathak, Tanmaya ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CURRENT TRENDS; CYCLOPROPANATION; DIASTEREOSELECTIVE; FUNCTIONALIZED; LEAVING GROUPS; RING CARBONS; STEREO-SELECTIVE; TERMINAL DOUBLE BONDS; VINYL SULFONES;

ATOMS; CARBOHYDRATES; PROPANE;

FABRICS;

CARBOHYDRATE; CARBON; CYCLOPROPANE; NUCLEOPHILE; SULFONE;

ARTICLE; CHEMICAL BOND; CYCLOPROPANATION; STEREOCHEMISTRY; SYNTHESIS;

CARBOHYDRATES; CARBON; CYCLOPROPANES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFONES;

EID: 64249104393     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802709q     Document Type: Article

References (57)

1. (a) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
2. (b) Kulinkovich, O. G. Chem. ReV. 2003, 103, 2597.
3. (c) Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321.
4. (d) von Angerer, S. In Carbocyclic Three- and Four-membered Ring Compounds. Methods of Organic Chemistry (Houben-Weyl); de Meijere, A., Ed.; Verlag: New York, 1997; Vol. E17c, pp 2121-2153.
5. Selected references on the synthetic applications of cyclopropanes: (a) Carson, C. A.; Kerr, M. A. Org. Lett. 2009, 11, 777.
6. (b) Leduc, A. B.; Kerr, M. A. Angew. Chem., Int. Ed. 2008, 47, 7945.
7. (c) Schall, A.; Reiser, O. Eur. J. Org. Chem. 2008, 14, 2353.
8. (d) Morales, C. L.; Pagenkopf, B. L. Org. Lett. 2008, 10, 157.
9. (e) Bajtos, B.; Yu, M.; Zhao, H.; Pagenkopf, B. L. J. Am. Chem. Soc. 2007, 129, 9631.
10. (f) Kalidindi, S.; Jeong, W. B.; Schall, A.; Bandichhor, R.; Nosse, B.; Reiser, O. Angew. Chem., Int. Ed. 2007, 46, 6361.
11. (g) Veljkovic, I.; Zimmer, R.; Reissig, H.-U.; Bruedgam, I.; Hartl, H. Synthesis 2006, 16, 2677.
12. (h) Aulenta, F.; Hoelemann, A.; Reissig, H.-U. Eur. J. Org. Chem. 2006, 7, 1733.
13. (i) Carson, C. A.; Kerr, M. A. J. Org. Chem. 2005, 70, 8242.
14. (j) AlHarrasi, A.; Reissig, H.-U. Synlett 2005, 15, 2376.
15. (k) Young, I. S.; Williams, J. L.; Kerr, M. A. Org. Lett. 2005, 7, 953.
16. (l) Gnad, F.; Poleschak, M.; Reiser, O. Tetrahedron Lett. 2004, 45, 4277.
17. (m) Yu, M.; Pantos, G. D.; Sessler, J. L.; Pagenkopf, B. L. Org. Lett. 2004, 6, 1057.
18. (n) Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023.
19. (o) Yu, M.; Pagenkopf, B. L. Org. Lett. 2003, 5, 5099.
20. (p) Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122.
21. (q) Gnad, F.; Reiser, O. Chem. ReV. 2003, 103, 1603.
22. (r) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
23. (s) Chhor, R. B.; Nosse, B.; Sorgel, S.; Bohm, C.; Seitz, M.; Reiser, O. Chem. Eur. J. 2003, 9, 260.
24. (t) England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704.
25. (u) Zimmer, R.; Ziemer, A.; Gruner, M.; Brudgam, I.; Hartl, H.; Reissig, H.-U. Synthesis 2001, 11, 1649.
26. (v) Yu, M.; Lynch, V.; Pagenkopf, B. L. Org. Lett. 2001, 3, 2563.
27. (w) Boehm, C.; Reiser, O. Org. Lett. 2001, 3, 1315.
28. (x) Khan, F. A.; Czerwonka, R.; Reissig, H.-U. Eur. J. Org. Chem. 2000, 21, 3607.
29. Weatherhead-Kloste, A. R.; Corey, E. J. Org. Lett. 2006, 8, 171.
30. (b) Zhu, S.; Ruppel, J. V.; Lu, H.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2008, 130, 5042.
31. (a) Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117.
32. Cousins, G. S.; Hoberg, J. O. Chem. Soc. ReV. 2000, 29, 165.
33. (a) Nowak, I.; Robins, M. J. J. Org. Chem. 2007, 72, 3319.
34. (b) Gagneron, J.; Gosselin, G.; Mathe, C. J. Org. Chem. 2005, 70, 6891.
35. (a) Corsaro, A.; Pistara, V.; Catelani, G.; D'Andrea, F.; Adamo, R.; Chiacchio, M. A. Tetrahedron Lett. 2006, 47, 6591.
36. (b) Charette, A. B.; Cote, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166.
37. (a) Zindel, J.; de Meijere, A. Synthesis 1994, 2, 190.
38. (b) Ogura, K.; Iihama, T.; Takahashi, K.; Iida, H. Bull. Chem. Soc. Jpn. 1984, 57, 3347.
39. (c) Gravel, D.; Leboeuf, C. Can. J. Chem. 1982, 60, 574.
40. (d) Eisch, J. J.; Galle, J. E. J. Org. Chem. 1979, 44, 3277.
41. For a review, see: Pathak, T. Tetrahedron 2008, 64, 3605.
42. (a) Diez, D.; Beneitez, M. T.; Marcos, I. S.; Garrido, N. M.; Basabe, P.; Sanz, F.; Broughton, H. B.; Urones, J. G. Org. Lett. 2003, 5, 4361.
43. (b) Diez, D.; Beneitez, M. T.; Marcos, I. S.; Garrido, N. M.; Basabe, P.; Urones, J. G. Tetrahedron: Asymmetry 2002, 13, 639.
44. Alonso-Cruz, C. R.; León, E. I.; Ortiz-López, F. J.; Rodr?́guez, M. S.; Suárez, E. Tetrahedron Lett. 2005, 46, 5265.
45. Yamashita, A.; Rosowsky, A. J. Org. Chem. 1976, 41, 3422.
46. Garciía Ruano, J. L.; Alonso de Diego, S. A.; Rosario, M. M.; Torrente, E.; Martín, C. A. M. Org. Lett. 2004, 6, 4945.
47. (a) Schank, K.; Abdel Wahab, A.-M. A.; Buegler, S.; Eigen, P.; Jager, J.; Jost, K. Tetrahedron 1994, 50, 3721.
48. (b) Lee, P. H.; Kim, J. S.; Youn, C.; Kim, S. Tetrahedron Lett. 1993, 34, 7583.
49. (c) Pohmakotr, M.; Ratchataphusit, J. Tetrahedron 1993, 49, 6473.
50. (d) Wienand, A.; Reissig, H.-U. Organometallics 1990, 9, 3133.
51. (e) Fedorynski, M.; Dybowska, A.; Jonczyk, A. Synthesis 1988, 7, 549.
52. (a) Cao, W.; Zhang, H.; Chen, J.; Zhou, X.; Shao, M.; McMills, M. C. Tetrahedron 2007, 64, 163.
53. (b) Reutrakul, V.; Jaratjaroonphong, J.; Tuchinda, P.; Kuhakarn, C.; Kongsaeree, P.; Prabpai, S.; Pohmakotr, M. Tetrahedron Lett. 2006, 47, 4753.
54. (c) Sebelius, S.; Olsson, V. J.; Szabo, K. J. J. Am. Chem. Soc. 2005, 127, 10478.
55. (d) Shi, W.; Zhang, B.; Zhang, J.; Liu, B.; Zhang, S.; Wang, J. Org. Lett. 2005, 7, 3103.
56. (e) Wang, Y.; Zhao, X.; Li, Y.; Lu, L. Tetrahedron Lett. 2004, 45, 7775.
57. (f) Papageorgiou, C. D.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2003, 42, 828.