Enantiospecific synthesis of substituted 1-norbornanesulfonic acids and 1-norbornanesulfenic and sulfonic acid derivatives

Tetrahedron Asymmetry

Volumn 11, Issue 8, 2000, Pages 1709-1717

  García Martínez, Antonio ^a   Teso Vilar, Enrique ^b   Moreno Jiménez, Florencio ^a   García Amo, María ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR; NATURAL PRODUCT; NORBORNANE DERIVATIVE; SULFENIC ACID DERIVATIVE; SULFONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; STEREOSPECIFICITY; SYNTHESIS;

EID: 0000208006     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00122-1     Document Type: Article

References (47)

1. For a review, see: Oppolzer, W. Tetrahedron 1987, 43, 1969-2004.
2. Knollmüller, M.; Ferencic, M.; Gärtner, P.; Mereiter, K.; Noe, C. R. Tetrahedron: Asymmetry 1998, 9, 4009-4020.
3. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. J. Org. Chem. 1999, 64, 2114-2118.
4. Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
5. Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832-4842.
6. Oppolzer, W. Pure Appl. Chem. 1990, 62, 1241-1250.
7. Kim, B.; Lee, J. Tetrahedron: Asymmetry 1991, 2, 1359-1370.
8. Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.; Qi, H.; Han, W.; Przeslawski, R. M.; Chem, B.-Ch.; Carrol, P. J. J. Org. Chem. 1998, 2273-2280.
9. Mizojiri, R.; Urabe, H.; Sato, F. Angew. Chem., Int. Ed. 1998, 37, 2666-2668.
10. Agócs, A.; Bényei, A.; Somogyi, L.; Herczegh, P. Tetrahedron: Asymmetry 1998, 9, 3359-3363.
11. Jezewski, A.; Chajewska, K.; Wielogórski, Z.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 1741-1749.
12. Fioravanti, S.; Loreto, M. A.; Pellacani, L.; Sabbatini, F.; Tardella, P. A. Tetrahedron: Asymmetry 1994, 5, 473-478.
13. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876-889.
14. Oppolzer, W.; Dudfield, P. Tetrahedron Lett. 1985, 26, 5037-5040.
15. Hernanz, D.; Camps, F.; Guerrero, A.; Delgado, A. Tetrahedron: Asymmetry 1995, 6, 2291-2298.
16. Davis, F. A.; Reddy, R. E.; Kasu, P. V. N.; Portonovo, P. S.; Carrol, P. J. J. Org. Chem. 1997, 62, 3625-3630.
17. Page, P. C. B.; Heer, J. P.; Bethell, D.; Lund, A.; Collington, E. W.; Andrews, D. M. J. Org. Chem. 1997, 62, 6093-6094.
18. Gala, D.; DiBenedetto, D. J. Tetrahedron: Asymmetry 1997, 8, 3047-3050.
19. Fitzpatrick, K.; Hulst, R.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1861-1864.
20. Hof, R. P.; Poelert, M. A.; Peper, N. C. M. W.; Kellogg, R. M. Tetrahedron: Asymmetry 1994, 5, 31-34.
21. Fiaud, J.-C.; Mazé, F.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 3647-3655.
22. Kang, J.; Kim, J. B.; Kim, J. W.; Lee, D. J. Chem. Soc., Perkin Trans. 2 1997, 189-194.
23. Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z. J. Org. Chem. 1996, 61, 489-493.
24. Aggarwal, V. K.; Thompson, A.; Jones, R. V. H.; Standen, M. Tetrahedron: Asymmetry 1995, 6, 2557-2564.
25. Aggarwal, V. K.; Ford, J. G.; Fonquerna, S.; Adams, H.; Jones, R. V. H.; Fieldhouse, R. J. Am. Chem. Soc. 1998, 120, 8328-8339.
26. Aggarwal, V. K.; Thompson, A.; Jones, R. V. H.; Standen, M. J. Org. Chem. 1996, 61, 8368-8369.
27. Yus, M.; Ramón, D. J. Tetrahedron: Asymmetry 1997, 8, 2479-2496.
28. Hwang, Ch.-D.; Uang, B.-J. Tetrahedron: Asymmetry 1998, 9, 3979-3984.
29. Yus, M.; Ramón, D. J. Tetrahedron Lett. 1998, 39, 1239-1242.
30. Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.; Pericás, M. A. J. Org. Chem. 1998, 63, 7037-7052 and references cited therein.
31. Yang, T.-K.; Chen, R.-Y.; Lee, D.-S.; Peng, W.-S.; Jiang, Y.-Z.; Mi, A.-Q.; Jong, T.-T. J. Org. Chem. 1994, 59, 914-921.
32. Agami, C.; Prince, B.; Puchot, C. Synth. Commun. 1990, 20, 3289-3294.
33. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates, and Resolutions; John Willey & Sons: New York, 1981; p. 260.
34. Koppenhoefer, B.; Völlenkle, H.; Brendle, H.-G.; Schwierskott, M. Synthesis 1997, 515-517.
35. Barret, A. G. M.; Braddock, D. C.; Christian, P. W. N.; Pilipauskas, D.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1998, 63, 5818-5823.
36. Clarck, R. D.; Kern, J. R.; Kurz, L. J.; Nelson, J. T. Heterocycles 1990, 31, 353-366.
37. Dai, X.; Wong, A.; Virgil, S. C. J. Org. Chem. 1998, 63, 2597-2600.
38. Chow, H.-F.; Wan, C.-W.; Ng, M.-K. J. Org. Chem. 1996, 61, 8712-8714.
39. Martínez, A. G.; Teso, E.; García, A.; Moya, S.; Martínez, P.; Subramanian, L. R. Tetrahedron: Asymmetry 1996, 7, 2177-2180.
40. Martínez, A. G.; Teso, E.; García, A.; Moya, S.; Martínez, P. Tetrahedron: Asymmetry 1998, 9, 1737-1745 and references cited therein.
41. Martínez, A. G.; Teso, E.; García, A.; Martínez, P.; Macías, R.; Martínez, M. P. Tetrahedron: Asymmetry 1999, 10, 1499-1505.
42. Martínez, A. G.; Teso, E.; García, A.; Moya, S.; Martínez, P. Rapid Commun. Mass Spectrom. 1999, 13, 1472-1476.
43. Martínez, A. G.; Vilar, E. T.; Jiménez, F. M.; Bilbao, C. M. Tetrahedron: Asymmetry 1997, 8, 3031-3034.
44. Martínez, A. G.; Teso, E.; Moya, S.; Osío Barcina, J.; Gómez, P. C. J. Org. Chem. 1999, 64, 5611-5619 and references cited therein.
45. (a) Funk, R. L.; Abelman, M. M. J. Org. Chem. 1986, 51, 3247-3248.
46. (b) Mann, B. E.; Baily, P. M.; Maitilis, P. M. J. Am. Chem. Soc. 1975, 1275-1276.
47. Mehta, G.; Murthy, A. N. J. Org. Chem. 1987, 52, 2875-2881.