Enantioselective synthesis of (+)-5,6-exo-(isopropylidendioxy)-2-phenylsulfonyl-7-oxabicyclo[2.2.1]hept-2-ene

Tetrahedron Asymmetry

Volumn 10, Issue 11, 1999, Pages 2237-2242

  Arjona, Odón ^a   Iradier, Fátima ^a   Medel, Rocío ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

5,6 EXO (ISOPROPYLIDENDIOXY) 2 PHENYLSULFONYL 7 OXABICYCLO[2.2.1]HEPT 2 ENE; FURAN; SULFONE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; PARTIAL DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033522728     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00217-7     Document Type: Article

References (25)

1. Aceña, J. L.; Arjona, O.; Iradier, F.; Plumet, J. Tetrahedron Lett. 1996, 37, 105-106.
2. Arjona, O.; Borrallo, C.; Iradier, F.; Medel, R.; Plumet, J. Tetrahedron Lett. 1998, 39, 1977-1980.
3. Aceña, J. L.; Arjona, O.; Plumet, J. Tetrahedron: Asymmetry 1996, 7, 3535-3544.
4. Arjona, O.; Iradier, F.; Martínez-Alcázar, M. P.; Cano, F. H.; Fonseca, I.; Plumet, J. Tetrahedron Lett. 1998, 39, 6741-6744.
5. For a general review on recent findings of cycloadditions in synthesis, see: (a) Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. (See pages 3884-3885 concerning the asymmetric Diels-Alder reactions.) For a review on synthetic applications of furan Diels-Alder chemistry, see: (b) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233. For reviews on the use of 7-oxanorbonenes in organic synthesis, see: (c) Viera, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871. (d) Reymond, J. L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729-736. (e) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185. (f) Corey, E. J.; Loh, J. L. Tetrahedron Lett. 1993, 34, 3979-3982. (g) Sevin, F.; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926. (h) Woo, S.; Keay, B. A. Synthesis 1996, 669-686. (i) Liu, P.; Lautens, M. Topics in Current Chemistry 1997, 190, 1-84.
6. For a general review on recent findings of cycloadditions in synthesis, see: (a) Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. (See pages 3884-3885 concerning the asymmetric Diels-Alder reactions.) For a review on synthetic applications of furan Diels-Alder chemistry, see: (b) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233. For reviews on the use of 7-oxanorbonenes in organic synthesis, see: (c) Viera, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871. (d) Reymond, J. L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729-736. (e) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185. (f) Corey, E. J.; Loh, J. L. Tetrahedron Lett. 1993, 34, 3979-3982. (g) Sevin, F.; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926. (h) Woo, S.; Keay, B. A. Synthesis 1996, 669-686. (i) Liu, P.; Lautens, M. Topics in Current Chemistry 1997, 190, 1-84.
7. For a general review on recent findings of cycloadditions in synthesis, see: (a) Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. (See pages 3884-3885 concerning the asymmetric Diels-Alder reactions.) For a review on synthetic applications of furan Diels-Alder chemistry, see: (b) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233. For reviews on the use of 7-oxanorbonenes in organic synthesis, see: (c) Viera, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871. (d) Reymond, J. L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729-736. (e) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185. (f) Corey, E. J.; Loh, J. L. Tetrahedron Lett. 1993, 34, 3979-3982. (g) Sevin, F.; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926. (h) Woo, S.; Keay, B. A. Synthesis 1996, 669-686. (i) Liu, P.; Lautens, M. Topics in Current Chemistry 1997, 190, 1-84.
8. For a general review on recent findings of cycloadditions in synthesis, see: (a) Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. (See pages 3884-3885 concerning the asymmetric Diels-Alder reactions.) For a review on synthetic applications of furan Diels-Alder chemistry, see: (b) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233. For reviews on the use of 7-oxanorbonenes in organic synthesis, see: (c) Viera, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871. (d) Reymond, J. L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729-736. (e) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185. (f) Corey, E. J.; Loh, J. L. Tetrahedron Lett. 1993, 34, 3979-3982. (g) Sevin, F.; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926. (h) Woo, S.; Keay, B. A. Synthesis 1996, 669-686. (i) Liu, P.; Lautens, M. Topics in Current Chemistry 1997, 190, 1-84.
9. For a general review on recent findings of cycloadditions in synthesis, see: (a) Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. (See pages 3884-3885 concerning the asymmetric Diels-Alder reactions.) For a review on synthetic applications of furan Diels-Alder chemistry, see: (b) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233. For reviews on the use of 7-oxanorbonenes in organic synthesis, see: (c) Viera, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871. (d) Reymond, J. L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729-736. (e) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185. (f) Corey, E. J.; Loh, J. L. Tetrahedron Lett. 1993, 34, 3979-3982. (g) Sevin, F.; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926. (h) Woo, S.; Keay, B. A. Synthesis 1996, 669-686. (i) Liu, P.; Lautens, M. Topics in Current Chemistry 1997, 190, 1-84.
10. For a general review on recent findings of cycloadditions in synthesis, see: (a) Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. (See pages 3884-3885 concerning the asymmetric Diels-Alder reactions.) For a review on synthetic applications of furan Diels-Alder chemistry, see: (b) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233. For reviews on the use of 7-oxanorbonenes in organic synthesis, see: (c) Viera, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871. (d) Reymond, J. L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729-736. (e) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185. (f) Corey, E. J.; Loh, J. L. Tetrahedron Lett. 1993, 34, 3979-3982. (g) Sevin, F.; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926. (h) Woo, S.; Keay, B. A. Synthesis 1996, 669-686. (i) Liu, P.; Lautens, M. Topics in Current Chemistry 1997, 190, 1-84.
11. For a general review on recent findings of cycloadditions in synthesis, see: (a) Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. (See pages 3884-3885 concerning the asymmetric Diels-Alder reactions.) For a review on synthetic applications of furan Diels-Alder chemistry, see: (b) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233. For reviews on the use of 7-oxanorbonenes in organic synthesis, see: (c) Viera, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871. (d) Reymond, J. L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729-736. (e) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185. (f) Corey, E. J.; Loh, J. L. Tetrahedron Lett. 1993, 34, 3979-3982. (g) Sevin, F.; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926. (h) Woo, S.; Keay, B. A. Synthesis 1996, 669-686. (i) Liu, P.; Lautens, M. Topics in Current Chemistry 1997, 190, 1-84.
12. For a general review on recent findings of cycloadditions in synthesis, see: (a) Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. (See pages 3884-3885 concerning the asymmetric Diels-Alder reactions.) For a review on synthetic applications of furan Diels-Alder chemistry, see: (b) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233. For reviews on the use of 7-oxanorbonenes in organic synthesis, see: (c) Viera, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871. (d) Reymond, J. L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729-736. (e) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185. (f) Corey, E. J.; Loh, J. L. Tetrahedron Lett. 1993, 34, 3979-3982. (g) Sevin, F.; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926. (h) Woo, S.; Keay, B. A. Synthesis 1996, 669-686. (i) Liu, P.; Lautens, M. Topics in Current Chemistry 1997, 190, 1-84.
13. For a general review on recent findings of cycloadditions in synthesis, see: (a) Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. (See pages 3884-3885 concerning the asymmetric Diels-Alder reactions.) For a review on synthetic applications of furan Diels-Alder chemistry, see: (b) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233. For reviews on the use of 7-oxanorbonenes in organic synthesis, see: (c) Viera, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871. (d) Reymond, J. L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729-736. (e) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185. (f) Corey, E. J.; Loh, J. L. Tetrahedron Lett. 1993, 34, 3979-3982. (g) Sevin, F.; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926. (h) Woo, S.; Keay, B. A. Synthesis 1996, 669-686. (i) Liu, P.; Lautens, M. Topics in Current Chemistry 1997, 190, 1-84.
14. For the use of optically pure ethylenic sulphoxides as 2π partners in furan Diels-Alder reactions, see, for instance: (a) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771-772. (b) Takayama, H.; Hayashi, K.; Takeuchi, Y.; Koizumi, T. Heterocycles 1986, 24, 2137-2140. (c) Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 3065-3072. (d) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75-90. (e) Aggarwal, V. K.; Drabowicz, J.; Grainger, R. S.; Gültekin, Z.; Lightowler, M.; Spargo, P. L. J. Org. Chem. 1995, 60, 4962-4963. (f) Yamakoshi, Y. N.; Ge, W. Y.; Sugita, J.; Okayama, K. Heterocycles 1996, 42, 129-133. For other asymmetric Diels-Alder reactions using furan as the 4π component, see: (g) Fraile, J. M.; García, J. I.; Gracia, D.; Mayoral, J. A.; Pires, E. J. Org. Chem. 1996, 61, 9479-9482. (h) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105.
15. For the use of optically pure ethylenic sulphoxides as 2π partners in furan Diels-Alder reactions, see, for instance: (a) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771-772. (b) Takayama, H.; Hayashi, K.; Takeuchi, Y.; Koizumi, T. Heterocycles 1986, 24, 2137-2140. (c) Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 3065-3072. (d) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75-90. (e) Aggarwal, V. K.; Drabowicz, J.; Grainger, R. S.; Gültekin, Z.; Lightowler, M.; Spargo, P. L. J. Org. Chem. 1995, 60, 4962-4963. (f) Yamakoshi, Y. N.; Ge, W. Y.; Sugita, J.; Okayama, K. Heterocycles 1996, 42, 129-133. For other asymmetric Diels-Alder reactions using furan as the 4π component, see: (g) Fraile, J. M.; García, J. I.; Gracia, D.; Mayoral, J. A.; Pires, E. J. Org. Chem. 1996, 61, 9479-9482. (h) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105.
16. For the use of optically pure ethylenic sulphoxides as 2π partners in furan Diels-Alder reactions, see, for instance: (a) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771-772. (b) Takayama, H.; Hayashi, K.; Takeuchi, Y.; Koizumi, T. Heterocycles 1986, 24, 2137-2140. (c) Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 3065-3072. (d) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75-90. (e) Aggarwal, V. K.; Drabowicz, J.; Grainger, R. S.; Gültekin, Z.; Lightowler, M.; Spargo, P. L. J. Org. Chem. 1995, 60, 4962-4963. (f) Yamakoshi, Y. N.; Ge, W. Y.; Sugita, J.; Okayama, K. Heterocycles 1996, 42, 129-133. For other asymmetric Diels-Alder reactions using furan as the 4π component, see: (g) Fraile, J. M.; García, J. I.; Gracia, D.; Mayoral, J. A.; Pires, E. J. Org. Chem. 1996, 61, 9479-9482. (h) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105.
17. For the use of optically pure ethylenic sulphoxides as 2π partners in furan Diels-Alder reactions, see, for instance: (a) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771-772. (b) Takayama, H.; Hayashi, K.; Takeuchi, Y.; Koizumi, T. Heterocycles 1986, 24, 2137-2140. (c) Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 3065-3072. (d) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75-90. (e) Aggarwal, V. K.; Drabowicz, J.; Grainger, R. S.; Gültekin, Z.; Lightowler, M.; Spargo, P. L. J. Org. Chem. 1995, 60, 4962-4963. (f) Yamakoshi, Y. N.; Ge, W. Y.; Sugita, J.; Okayama, K. Heterocycles 1996, 42, 129-133. For other asymmetric Diels-Alder reactions using furan as the 4π component, see: (g) Fraile, J. M.; García, J. I.; Gracia, D.; Mayoral, J. A.; Pires, E. J. Org. Chem. 1996, 61, 9479-9482. (h) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105.
18. For the use of optically pure ethylenic sulphoxides as 2π partners in furan Diels-Alder reactions, see, for instance: (a) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771-772. (b) Takayama, H.; Hayashi, K.; Takeuchi, Y.; Koizumi, T. Heterocycles 1986, 24, 2137-2140. (c) Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 3065-3072. (d) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75-90. (e) Aggarwal, V. K.; Drabowicz, J.; Grainger, R. S.; Gültekin, Z.; Lightowler, M.; Spargo, P. L. J. Org. Chem. 1995, 60, 4962-4963. (f) Yamakoshi, Y. N.; Ge, W. Y.; Sugita, J.; Okayama, K. Heterocycles 1996, 42, 129-133. For other asymmetric Diels-Alder reactions using furan as the 4π component, see: (g) Fraile, J. M.; García, J. I.; Gracia, D.; Mayoral, J. A.; Pires, E. J. Org. Chem. 1996, 61, 9479-9482. (h) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105.
19. For the use of optically pure ethylenic sulphoxides as 2π partners in furan Diels-Alder reactions, see, for instance: (a) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771-772. (b) Takayama, H.; Hayashi, K.; Takeuchi, Y.; Koizumi, T. Heterocycles 1986, 24, 2137-2140. (c) Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 3065-3072. (d) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75-90. (e) Aggarwal, V. K.; Drabowicz, J.; Grainger, R. S.; Gültekin, Z.; Lightowler, M.; Spargo, P. L. J. Org. Chem. 1995, 60, 4962-4963. (f) Yamakoshi, Y. N.; Ge, W. Y.; Sugita, J.; Okayama, K. Heterocycles 1996, 42, 129-133. For other asymmetric Diels-Alder reactions using furan as the 4π component, see: (g) Fraile, J. M.; García, J. I.; Gracia, D.; Mayoral, J. A.; Pires, E. J. Org. Chem. 1996, 61, 9479-9482. (h) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105.
20. For the use of optically pure ethylenic sulphoxides as 2π partners in furan Diels-Alder reactions, see, for instance: (a) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771-772. (b) Takayama, H.; Hayashi, K.; Takeuchi, Y.; Koizumi, T. Heterocycles 1986, 24, 2137-2140. (c) Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 3065-3072. (d) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75-90. (e) Aggarwal, V. K.; Drabowicz, J.; Grainger, R. S.; Gültekin, Z.; Lightowler, M.; Spargo, P. L. J. Org. Chem. 1995, 60, 4962-4963. (f) Yamakoshi, Y. N.; Ge, W. Y.; Sugita, J.; Okayama, K. Heterocycles 1996, 42, 129-133. For other asymmetric Diels-Alder reactions using furan as the 4π component, see: (g) Fraile, J. M.; García, J. I.; Gracia, D.; Mayoral, J. A.; Pires, E. J. Org. Chem. 1996, 61, 9479-9482. (h) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105.
21. For the use of optically pure ethylenic sulphoxides as 2π partners in furan Diels-Alder reactions, see, for instance: (a) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771-772. (b) Takayama, H.; Hayashi, K.; Takeuchi, Y.; Koizumi, T. Heterocycles 1986, 24, 2137-2140. (c) Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1990, 3065-3072. (d) Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75-90. (e) Aggarwal, V. K.; Drabowicz, J.; Grainger, R. S.; Gültekin, Z.; Lightowler, M.; Spargo, P. L. J. Org. Chem. 1995, 60, 4962-4963. (f) Yamakoshi, Y. N.; Ge, W. Y.; Sugita, J.; Okayama, K. Heterocycles 1996, 42, 129-133. For other asymmetric Diels-Alder reactions using furan as the 4π component, see: (g) Fraile, J. M.; García, J. I.; Gracia, D.; Mayoral, J. A.; Pires, E. J. Org. Chem. 1996, 61, 9479-9482. (h) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105.
22. De Lucchi, O.; Marchiero, C.; Valle, G.; Modena, G. J. Chem. Soc., Chem. Commun. 1985, 878-880. In this paper, the authors describe the reaction between a diastereomeric mixture of 3 and cyclopentadiene.
23. 3) was isolated from the mixture in 75% yield as previously described. The absolute configuration of (+)-3 remains unknown.
24. Wagner, J.; Viera, E.; Vogel, P. Helv. Chim. Acta 1988, 71, 624-630.
25. 3). See Ref. 4.