Desymmetrization of 1,4-dien-3-ols and related compounds via Ueno-Stork radical cyclizations

Organic Letters

Volumn 2, Issue 8, 2000, Pages 1061-1063

  Villar, Félix ^a   Equey, Olivier ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001739718     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005613v     Document Type: Article

References (34)

1. For general reviews on desymmetrization reactions, see: Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765-1784. Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9-17. Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213.
2. For general reviews on desymmetrization reactions, see: Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765-1784. Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9-17. Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213.
3. For general reviews on desymmetrization reactions, see: Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765-1784. Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9-17. Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213.
4. For desymmetrization of 1,4-dien-3-ols and related compounds via Sharpless epoxidation, see: Smith, D. B.; Wan, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793-4808. Jäger, V.; Schröter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195-2210. Hatekeyama, S.; Sakurai, K.; Numata H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201-5203. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber; S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601. Okamoto, S.; Kobayashi, Y.; Kato, H.; Hori, K.; Takahashi, T.; Tsuji, J.; Sato, F. J. Org. Chem. 1988, 53, 5590-5592. Burke, S. D.; Buchanan, J. L.; Rovin, D. L. Tetrahedron Lett. 1991, 32, 3961-3964. Belley, M. L.; Hill, B.; Mitenko, M.; Scheigetz, J.; Zamboni, R. Synlett 1996, 92-94. Via hydrosilylation: Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333-7336.
5. For desymmetrization of 1,4-dien-3-ols and related compounds via Sharpless epoxidation, see: Smith, D. B.; Wan, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793-4808. Jäger, V.; Schröter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195-2210. Hatekeyama, S.; Sakurai, K.; Numata H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201-5203. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber; S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601. Okamoto, S.; Kobayashi, Y.; Kato, H.; Hori, K.; Takahashi, T.; Tsuji, J.; Sato, F. J. Org. Chem. 1988, 53, 5590-5592. Burke, S. D.; Buchanan, J. L.; Rovin, D. L. Tetrahedron Lett. 1991, 32, 3961-3964. Belley, M. L.; Hill, B.; Mitenko, M.; Scheigetz, J.; Zamboni, R. Synlett 1996, 92-94. Via hydrosilylation: Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333-7336.
6. For desymmetrization of 1,4-dien-3-ols and related compounds via Sharpless epoxidation, see: Smith, D. B.; Wan, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793-4808. Jäger, V.; Schröter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195-2210. Hatekeyama, S.; Sakurai, K.; Numata H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201-5203. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber; S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601. Okamoto, S.; Kobayashi, Y.; Kato, H.; Hori, K.; Takahashi, T.; Tsuji, J.; Sato, F. J. Org. Chem. 1988, 53, 5590-5592. Burke, S. D.; Buchanan, J. L.; Rovin, D. L. Tetrahedron Lett. 1991, 32, 3961-3964. Belley, M. L.; Hill, B.; Mitenko, M.; Scheigetz, J.; Zamboni, R. Synlett 1996, 92-94. Via hydrosilylation: Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333-7336.
7. For desymmetrization of 1,4-dien-3-ols and related compounds via Sharpless epoxidation, see: Smith, D. B.; Wan, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793-4808. Jäger, V.; Schröter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195-2210. Hatekeyama, S.; Sakurai, K.; Numata H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201-5203. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber; S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601. Okamoto, S.; Kobayashi, Y.; Kato, H.; Hori, K.; Takahashi, T.; Tsuji, J.; Sato, F. J. Org. Chem. 1988, 53, 5590-5592. Burke, S. D.; Buchanan, J. L.; Rovin, D. L. Tetrahedron Lett. 1991, 32, 3961-3964. Belley, M. L.; Hill, B.; Mitenko, M.; Scheigetz, J.; Zamboni, R. Synlett 1996, 92-94. Via hydrosilylation: Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333-7336.
8. For desymmetrization of 1,4-dien-3-ols and related compounds via Sharpless epoxidation, see: Smith, D. B.; Wan, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793-4808. Jäger, V.; Schröter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195-2210. Hatekeyama, S.; Sakurai, K.; Numata H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201-5203. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber; S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601. Okamoto, S.; Kobayashi, Y.; Kato, H.; Hori, K.; Takahashi, T.; Tsuji, J.; Sato, F. J. Org. Chem. 1988, 53, 5590-5592. Burke, S. D.; Buchanan, J. L.; Rovin, D. L. Tetrahedron Lett. 1991, 32, 3961-3964. Belley, M. L.; Hill, B.; Mitenko, M.; Scheigetz, J.; Zamboni, R. Synlett 1996, 92-94. Via hydrosilylation: Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333-7336.
9. For desymmetrization of 1,4-dien-3-ols and related compounds via Sharpless epoxidation, see: Smith, D. B.; Wan, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793-4808. Jäger, V.; Schröter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195-2210. Hatekeyama, S.; Sakurai, K.; Numata H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201-5203. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber; S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601. Okamoto, S.; Kobayashi, Y.; Kato, H.; Hori, K.; Takahashi, T.; Tsuji, J.; Sato, F. J. Org. Chem. 1988, 53, 5590-5592. Burke, S. D.; Buchanan, J. L.; Rovin, D. L. Tetrahedron Lett. 1991, 32, 3961-3964. Belley, M. L.; Hill, B.; Mitenko, M.; Scheigetz, J.; Zamboni, R. Synlett 1996, 92-94. Via hydrosilylation: Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333-7336.
10. For desymmetrization of 1,4-dien-3-ols and related compounds via Sharpless epoxidation, see: Smith, D. B.; Wan, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793-4808. Jäger, V.; Schröter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195-2210. Hatekeyama, S.; Sakurai, K.; Numata H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201-5203. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber; S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601. Okamoto, S.; Kobayashi, Y.; Kato, H.; Hori, K.; Takahashi, T.; Tsuji, J.; Sato, F. J. Org. Chem. 1988, 53, 5590-5592. Burke, S. D.; Buchanan, J. L.; Rovin, D. L. Tetrahedron Lett. 1991, 32, 3961-3964. Belley, M. L.; Hill, B.; Mitenko, M.; Scheigetz, J.; Zamboni, R. Synlett 1996, 92-94. Via hydrosilylation: Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333-7336.
11. For desymmetrization of 1,4-dien-3-ols and related compounds via Sharpless epoxidation, see: Smith, D. B.; Wan, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793-4808. Jäger, V.; Schröter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195-2210. Hatekeyama, S.; Sakurai, K.; Numata H.; Ochi, N.; Takano, S. J. Am. Chem. Soc. 1988, 110, 5201-5203. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber; S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601. Okamoto, S.; Kobayashi, Y.; Kato, H.; Hori, K.; Takahashi, T.; Tsuji, J.; Sato, F. J. Org. Chem. 1988, 53, 5590-5592. Burke, S. D.; Buchanan, J. L.; Rovin, D. L. Tetrahedron Lett. 1991, 32, 3961-3964. Belley, M. L.; Hill, B.; Mitenko, M.; Scheigetz, J.; Zamboni, R. Synlett 1996, 92-94. Via hydrosilylation: Tamao, K.; Tohma, T.; Inui, N.; Nakayama, O.; Ito, Y. Tetrahedron Lett. 1990, 31, 7333-7336.
12. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199-202. Curran, D. P.; Qi, H.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 8430-8431. Curran, D. P.; Lin, C.-H.; DeMello, N. C.; Junggebauer, J. J. Am. Chem. Soc. 1994, 116, 8430-8431.
13. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199-202. Curran, D. P.; Qi, H.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 8430-8431. Curran, D. P.; Lin, C.-H.; DeMello, N. C.; Junggebauer, J. J. Am. Chem. Soc. 1994, 116, 8430-8431.
14. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199-202. Curran, D. P.; Qi, H.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 8430-8431. Curran, D. P.; Lin, C.-H.; DeMello, N. C.; Junggebauer, J. J. Am. Chem. Soc. 1994, 116, 8430-8431.
15. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1986, 1351-1356. Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742. Stork, G.; Sher, P. M.; Chen H-L. J. Am. Chem. Soc. 1986, 108, 6384-6385. Stork, G. Bull. Chem Soc. Jpn. 1988, 61, 149-154. Stork, G. Bull. Soc. Chim. Fr. 1990, 127, 675-680.
16. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1986, 1351-1356. Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742. Stork, G.; Sher, P. M.; Chen H-L. J. Am. Chem. Soc. 1986, 108, 6384-6385. Stork, G. Bull. Chem Soc. Jpn. 1988, 61, 149-154. Stork, G. Bull. Soc. Chim. Fr. 1990, 127, 675-680.
17. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1986, 1351-1356. Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742. Stork, G.; Sher, P. M.; Chen H-L. J. Am. Chem. Soc. 1986, 108, 6384-6385. Stork, G. Bull. Chem Soc. Jpn. 1988, 61, 149-154. Stork, G. Bull. Soc. Chim. Fr. 1990, 127, 675-680.
18. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1986, 1351-1356. Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742. Stork, G.; Sher, P. M.; Chen H-L. J. Am. Chem. Soc. 1986, 108, 6384-6385. Stork, G. Bull. Chem Soc. Jpn. 1988, 61, 149-154. Stork, G. Bull. Soc. Chim. Fr. 1990, 127, 675-680.
19. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1986, 1351-1356. Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742. Stork, G.; Sher, P. M.; Chen H-L. J. Am. Chem. Soc. 1986, 108, 6384-6385. Stork, G. Bull. Chem Soc. Jpn. 1988, 61, 149-154. Stork, G. Bull. Soc. Chim. Fr. 1990, 127, 675-680.
20. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Chem. Soc., Perkin Trans. 1 1986, 1351-1356. Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742. Stork, G.; Sher, P. M.; Chen H-L. J. Am. Chem. Soc. 1986, 108, 6384-6385. Stork, G. Bull. Chem Soc. Jpn. 1988, 61, 149-154. Stork, G. Bull. Soc. Chim. Fr. 1990, 127, 675-680.
21. Villar, F.; Renaud, P. Tetrahedron Lett. 1998, 39, 8655-8658.
22. Villar, F.; Andrey, O.; Renaud, P. Tetrahedron Lett. 1999, 40, 3375-3378.
23. 2O). Procedure D: A solution of (2-methoxycarbonylpropenyl)tributylstannane (1.55 g, 4 mmol), AIBN (4 mg), and the haloacetal (0.5 mmol) in benzene (5.5 mL) was heated under reflux. The reaction was monitored by TLC until all starting material disappeared. Workup as in procedure A.
24. The diastereoselectivity is expressed as % ds, the percentage of a certain diastereomer in a mixture of two or more diastereomers: Seebach, D.; Imwinkelried, R.; Weber, T. In Modern Synthetic Methods 1986; Scheffold, R., Ed.; Springer: Berlin, 1986; pp 125-259.
25. For the Beckwith-Houk transition state model, see: (a) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
26. (b) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959-974. For a discussion of the stereochemistry in Ueno-Stork cyclization reactions controlled by the acetal center, see refs 5 and 6 and: Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144-5153.
27. (b) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959-974. For a discussion of the stereochemistry in Ueno-Stork cyclization reactions controlled by the acetal center, see refs 5 and 6 and: Beckwith, A. L. J.; Page, D. M. J. Org. Chem. 1998, 63, 5144-5153.
28. The importance of the anomeric effect in Ueno-Stork radical cyclization has already been studied by Fraser-Reid in carbohydrate derivatives: Lopez, J.-C.; Gomez, A. M.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1994, 1533-1534. Lopez, J.-C.; Gomez, A. M.; Fraser-Reid, B. Aust. J. Chem. 1995, 48, 333-352. Lopez, J.-C.; Fraser-Reid, B. Chem. Commun. 1997, 2251-2257.
29. The importance of the anomeric effect in Ueno-Stork radical cyclization has already been studied by Fraser-Reid in carbohydrate derivatives: Lopez, J.-C.; Gomez, A. M.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1994, 1533-1534. Lopez, J.-C.; Gomez, A. M.; Fraser-Reid, B. Aust. J. Chem. 1995, 48, 333-352. Lopez, J.-C.; Fraser-Reid, B. Chem. Commun. 1997, 2251-2257.
30. The importance of the anomeric effect in Ueno-Stork radical cyclization has already been studied by Fraser-Reid in carbohydrate derivatives: Lopez, J.-C.; Gomez, A. M.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1994, 1533-1534. Lopez, J.-C.; Gomez, A. M.; Fraser-Reid, B. Aust. J. Chem. 1995, 48, 333-352. Lopez, J.-C.; Fraser-Reid, B. Chem. Commun. 1997, 2251-2257.
31. Isolation: Vigneron, J.-P.; Méric, R.; Larchevêque, M.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Synthesis using a Ueno-Stork radical cyclization: Itoh, T.; Sakabe, K.; Kudo, K.; Zagatti, P.; Renou, M. Tetrahedron Lett. 1998, 39, 4071-4074.
32. Isolation: Vigneron, J.-P.; Méric, R.; Larchevêque, M.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Synthesis using a Ueno-Stork radical cyclization: Itoh, T.; Sakabe, K.; Kudo, K.; Zagatti, P.; Renou, M. Tetrahedron Lett. 1998, 39, 4071-4074.
33. Villar, F.; Renaud, P. Manuscript in preparation.
34. Recently, Beckwith has observed a similar trans relationship in a related 6-exo-cyclization reaction; see ref 10.