Understanding the unusual regioselectivity in the nucleophilic ring-opening reactions of gem-disubstituted cyclic sulfates. Experimental and theoretical studies

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4506-4513

  Avenoza, Alberto ^a   Busto, Jesús H ^a   Corzana, Francisco ^a   García, José I ^b   Peregrina, Jesús M ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; ESTERS; ORGANIC SOLVENTS;

RING-OPENING REACTIONS;

SULFUR COMPOUNDS;

SODIUM AZIDE; SULFATE;

ARTICLE; CALCULATION; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037764769     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034178q     Document Type: Article

References (45)

1. Lohray, B. B. Synthesis 1992, 1035-1052.
2. Bittman, R.; Byun, H.-S.; He, L. Tetrahedron 2000, 56, 7051-7091.
3. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
4. Lohray, B. B.; Bhushan, V. Adv. Heterocycl. Chem. 1997, 68, 89-180.
5. (a) Hannun, Y. Science 1996, 274, 1855-1859.
6. (b) Byun, H.-S.; Bittman, R. In Phospholipids Handbook; Cevc, G., Ed.; Marcel Dekker: New York, 1993; pp 97-140.
7. (c) Lister, M. D.; Ruan, Z.-S.; Bittman, R. Biochim. Biophys. Acta 1995, 1256, 25-30.
8. (d) Byun, H.-S.; Sadlofsky, J. A.; Bittman, R. J. Org. Chem. 1998, 63, 2560-2563.
9. (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824.
10. (b) Noyori, R. Chem. Soc. Rev. 1989, 18, 187-208.
11. (c) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
12. (d) Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Org. Chem. 1984, 49, 555-557.
13. (e) Corey, E. J. Pure Appl. Chem. 1990, 62, 1209-1216.
14. (a) Sharpless, K. B.; Bruncko, M.; Schlingloff, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486.
15. (b) Sharpless, K. B.; Tao, B.; Schlingloff, G. Tetrahedron Lett. 1998, 39, 2507-2510.
16. (c) Song, C. E.; Oh, C. R.; Roh, E. J.; Lee, S.; Choi, J. H. Tetrahedron: Asymmetry 1999, 10, 671-674.
17. (d) O'Brien, P. Angew. Chem., Int. Ed. 1999, 38, 326-329.
18. (e) Bodkin, J. A.; McLeod, M. D. J. Chem. Soc., Perkin Trans. 1 2002, 2733-2746.
19. (a) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655-658.
20. (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 1998, 63, 5696-5699.
21. (c) Parkes, K. E. B.; Bushnell, D. J.; Crackett, P. H.; Dunsdon, S. J.; Freeman, A. C.; Gunn, M. P.; Hopkins, R. A.; Lambert, R. W.; Martin, J. A.; Merrett, J. H.; Redshaw, S.; Spurden, W. C.; Thomas, G. J. J. Org. Chem. 1994, 59, 3656-3664.
22. (d) Yokumatsu, T.; Suemune, K.; Shibuya, S. Heterocycles 1993, 35, 577-580.
23. (e) Hoffmann, R. W.; Stiasny, H. C. Tetrahedron Lett. 1995, 36, 4595-4598.
24. (f) Hoye, T. R.; Crawford, K. B. J. Org. Chem. 1994, 59, 520-522.
25. (a) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 4435-4436.
26. (b) Saito, S.; Takahashi, N.; Ishikawa, T.; Moriwaka, T. Tetrahedron Lett. 1991, 32, 667-670.
27. (c) Righi, G.; Rumboldt, G.; Bonini, C. J. Org. Chem. 1996, 61, 3557-3560.
28. Xiong, C.; Wang, W.; Hruby, V. J. J. Org. Chem. 2002, 67, 3514-3517.
29. Shao, H.; Rueter, J. K.; Goodman, M. J. Org. Chem. 1998, 63, 5240-5244.
30. Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Sucunza, D.; Zurbano, M. M. Tetrahedron: Asymmetry 2001, 12, 949-957.
31. (a) Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 37, 785-789.
32. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millan, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaroni, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; González, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Replogle, E. S.; Pople, J. A. Gaussian98, Revisions A.7 and A. 11; Gaussian, Inc.: Pittsburgh, PA, 1998.
34. Bauschlicher, C. W., Jr. Chem. Phys. Lett. 1995, 246, 40-44.
35. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098-16104.
36. Ruiz-López, M. F.; Assfeld, X.; García, J. I.; Mayoral, J. A.; Salvatella L. J. Am. Chem. Soc. 1993, 115, 8780-8787.
37. (a) Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211-7218.
38. (b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
39. (c) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
40. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
41. Bennani, Y. L.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 2079-2082.
42. (a) Lopez, X.; Dejaegere, A.; Karplus, M. J. Am. Chem. Soc. 2001, 123, 11755-11763.
43. (b) Lopez, X.; Dejaegere, A.; Karplus, M. J. Am. Chem. Soc. 1999, 121, 5548-5558.
44. Assfeld, X.; Ruiz-López, M. F.; Garcia, J. I.; Mayoral, J. A.; Salvatella, L. J. Chem. Soc., Chem. Commun. 1995, 1371-1372.
45. Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351-361.