Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides

Journal of Organic Chemistry

Volumn 76, Issue 8, 2011, Pages 2532-2547

  Alberch, Laura ^a   Cheng, Gang ^a   Seo, Seung Kee ^a   Li, Xuehua ^a   Boulineau, Fabien P ^a   Wei, Alexander ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERICS; DFT CALCULATION; DIMETHYLDIOXIRANE; FRONTIER MOLECULAR ORBITALS; GLYCALS; MAJORITY RULE; PYRANOSIDES; STEREO-SELECTIVE; VARIABLE EFFECTS;

DYNAMIC POSITIONING; MOLECULAR ORBITALS; STEREOSELECTIVITY;

MOLECULAR OXYGEN;

4 DEOXYPENTENOSIDE; CARBOHYDRATE DERIVATIVE; DIMETHYLDIOXIRANE; EPOXIDE; GLYCAL; OXYGEN; PYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; EPOXIDATION; FACIOSELECTIVITY; STEREOCHEMISTRY;

CARBON; ELECTRONS; EPOXY COMPOUNDS; GLYCOSIDES; OXYGEN; STEREOISOMERISM;

EID: 79953894875     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102382r     Document Type: Article

References (63)

1. Tolstikov, A. G.; Tolstikov, G. A. Russ. Chem. Rev. 1993, 62 (6) 579-601
2. Ferrier, R. J.; Hoberg, J. O. In Advances in Carbohydrate Chemistry and Biochemistry; Horton, D., Ed.; Academic Press: New York, 2003; Vol. 58, pp 55 - 119.
3. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380-1419
4. Plante, O. J.; Andrade, R. B.; Seeberger, P. H. Org. Lett. 1999, 1, 211-214
5. Cheshev, P.; Marra, A.; Dondoni, A. Carbohydr. Res. 2006, 341, 2714-2716
6. Koester, D. C.; Leibeling, M.; Neufeld, R.; Werz, D. B. Org. Lett. 2010, 12, 3934-3937
7. Examples of nonpyranoid glycals: Singh, I.; Seitz, O. Org. Lett. 2006, 8, 4319-4322
8. Markad, S.; Xia, S.; Surana, B.; Morton, M. D.; Hadad, C. M.; Peczuh, M. W. J. Org. Chem. 2008, 73, 6341-6354
9. Saha, J.; Peczuh, M. W. Org. Lett. 2009, 11, 4482-4484
10. Brigl, P. Hoppe-Seyler's Z. Physiol. Chem. 1921, 116, 1
11. Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666
12. Selected examples: Leeuwenburgh, M. A.; Timmers, C. M.; van der Marel, G. A.; van Boom, J. H.; Mallet, J.-M.; Sinaÿ, P. G. Tetrahedron Lett. 1997, 38, 6251-6254
13. Rainier, J. D.; Cox, J. M. Org. Lett. 2000, 2, 2707-2709
14. Parrish, J. D.; Little, R. D. Org. Lett. 2002, 4, 1439-1442
15. Boulineau, F. P.; Wei, A. J. Org. Chem. 2004, 69, 3391-3399
16. Wipf, P.; Pierce, J. G.; Zhuang, N. Org. Lett. 2005, 7, 483-485
17. Randolph, J. T.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5693-5700
18. Selected examples: Hayward, M. M.; Roth, R. M.; Duffy, K. J.; Dalko, P. I.; Stevens, K. L.; Guo, J.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 190-196
19. Johnson, H. W. B.; Majumder, U.; Rainier, J. D. J. Am. Chem. Soc. 2004, 127, 848-849
20. Potuzak, J. S.; Moilanen, S. B.; Tan, D. S. J. Am. Chem. Soc. 2005, 127, 13796-13797
21. Akoto, C. O.; Rainier, J. D. Angew. Chem., Int. Ed. 2008, 47, 8055-8058
22. Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281-2283
23. Cheng, G.; Boulineau, F. P.; Liew, S.-T.; Shi, Q.; Wenthold, P. G.; Wei, A. Org. Lett. 2006, 8, 4545-4548
24. It should be noted that protecting groups can affect the facioselectivity of DMDO oxidation (e.g., see ref 5), but this is beyond the scope of the present study.
25. Cheng, G.; Fan, R.-H.; Hernández-Torres, J.-M.; Boulineau, F. P.; Wei, A. Org. Lett. 2007, 8, 4849-4852
26. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994.
27. Huang, X. L.; Dannenberg, J. J.; Duran, M.; Bertrán, J. J. Am. Chem. Soc. 1993, 115, 4024-4030
28. Franck, R. W.; Kaila, N.; Blumenstein, M.; Geer, A.; Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1993, 58, 5335-5337
29. Boschi, A.; Chiappe, C.; De Rubertis, A.; Ruasse, M. F. J. Org. Chem. 2000, 65, 8470-8477
30. Dannenberg, J. J. Chem. Rev. 1999, 99, 1225-1241
31. Houk, K. N.; Liu, J.; DeMello, N. C.; Condroski, K. R. J. Am. Chem. Soc. 1997, 119, 10147-10152
32. Jenson, C.; Liu, J.; Houk, K. N.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 12982-12983
33. Bach, R. D.; Dmitrenko, O.; Adam, W.; Schambony, S. J. Am. Chem. Soc. 2002, 125, 924-934
34. Orendt, A. M.; Roberts, S. W.; Rainier, J. D. J. Org. Chem. 2006, 71, 5565-5573
35. Düfert, A.; Werz, D. B. J. Org. Chem. 2008, 73, 5514-5519
36. Jackel, C.; Dotz, H. J. Organomet. Chem. 2001, 624, 172-185
37. Halcomb, R.; Boyer, S.; Wittman, M.; Olson, S.; Denhart, D.; Liu, K.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5720-5749
38. Wittman, M.; Halcomb, R.; Danishefsky, S. J. Org. Chem. 1990, 55, 1979-1981
39. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 16, 1574-1585
40. Braithwaite, D. H.; Holzapfel, C. W.; Williams, D. B. G. S. Afr. J. Chem. 1998, 51, 162-164
41. Hernández-Torres, J. M.; Achkar, J.; Wei, A. J. Org. Chem. 2004, 69, 7206-7211
42. Fraser-Reid, B.; Radatus, B. J. Am. Chem. Soc. 1970, 92, 6661-6663
43. Fraser-Reid, B.; Tam, S. Y.-K.; Radatus, B. Can. J. Chem. 1975, 53, 2005-2016
44. Greenspoon, N.; Keinan, E. J. Org. Chem. 1988, 53, 3723-3731
45. Sasaki, K.; Wakamatsu, T.; Matsumura, S.; Toshima, K. Tetrahedron Lett. 2006, 47, 8271-8274
46. Davis, N. J.; Flitsch, S. L. Tetrahedron Lett. 1993, 34, 1181-1184
47. van den Bos, L.; Codée, J. D. C.; van der Toorn, J. C.; Boltje, T. J.; van Boom, J. H.; Overkleeft, H. S.; van der Marel, G. A. Org. Lett. 2004, 6, 2165-2168
48. Abdulla, R. F.; Brinkmeyer, R. S. Tetrahedron 1979, 35, 1675
49. Whistler, R. L.; Wolfrom, M. L. In Methods in Carbohydrate Chemistry; Academic Press: New York, 1962; Vol. I, pp 85 and 184.
50. Tolstikov, A. G.; Khakhalina, N. V.; Spirikhin, L. V. Synthesis 1988, 221-222
51. Chmielewskia, M.; Foktb, I.; Grodnera, J.; Grynkiewiczc, G.; Szeja, W. J. Carbohydr. Chem. 1989, 735-744
52. Adam, W.; Saha-Möller, C. R.; Zhao, C. G. In Organic Reactions; John Wiley & Sons, Inc.: New York, 2004; Vol. 61, pp 219 - 561.
53. Gibert, M.; Ferrer, M.; Sánchez-Baeza, F.; Messeguer, A. Tetrahedron Lett. 1997, 53, 8643-8650
54. Stevenin, A.; Boyer, F.; Beau, J.-M. J. Org. Chem. 2010, 75, 1783-1786
55. Mycock, D. K.; Sherlock, A. E.; Glossop, P. A.; Hayes, C. J. Tetrahedron Lett. 2008, 49, 6390-6392
56. DMDO oxidation of a gulal derivative similar to 6 was reported to proceed with 1:1 facioselectivity at 0 °C; see ref 5.
57. Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783-2792
58. N2 mechanism.
59. Jackel, C.; Dotz, H. J. Organomet. Chem. 2001, 624, 172-185
60. Wittman, M.; Halcomb, R.; Danishefsky, S. J. Org. Chem. 1990, 55, 1979-1981
61. Halcomb, R.; Boyer, S.; Wittman, M.; Olson, S.; Denhart, D.; Liu, K.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5720-5749
62. Kihlberg, J.; Frejd, T.; Jansson, K.; Magnusson, G. Carbohydr. Res. 1986, 152, 113-130
63. Mori, Y.; Morishima, N. Bull. Chem. Soc. Jpn. 1993, 66, 2061-2067