Enantioselective preparation of 4-substituted cyclohexenes by radical fragmentation of sulfoxides

Organic Letters

Volumn 1, Issue 6, 1999, Pages 873-875

  Imboden, Christoph ^a   Villar, Félix ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000418510     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990859p     Document Type: Article

References (30)

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11. For an early synthetic application of the radical fragmention of β-sulfinylated radicals, see: Miyamato, N.; Furuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 503-504. For a recent application to the preparation of allenes, see: Delouvrié, B.; Lacôte, E.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1999, 40, 3565-3568.
12. For an early synthetic application of the radical fragmention of β-sulfinylated radicals, see: Miyamato, N.; Furuoka, D.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 503-504. For a recent application to the preparation of allenes, see: Delouvrié, B.; Lacôte, E.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1999, 40, 3565-3568.
13. For an application in asymmetric synthesis, see: (a) Malacria, M.; Lacôte, E.; Delouvrié, B.; Fensterbank, L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2116-2118. For a related example based on sulfimide, see:
14. (b) Clark, A. J.; Rooke, S.; Sparey, T. J.; Taylor, P. C. Tetrahedron Lett. 1996, 37, 909-912.
15. The diastereoselectivity of hydrogen transfer has not been investigated in a systematic fashion. For an isolated example of diastereoselective hydrogen transfer, see: Bogen, S.; Malacria, M. J. Am. Chem. Soc. 1996, 118, 3992-3993.
16. Imboden, C.; Renaud, P. Tetrahedron: Asymmetry 1999, 10, 1051-1060.
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18. For a recent review on the use of Lewis acids in radical reaction, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562-2579. For the use of Lewis acids in radical reactions involving sulfoxides, see ref 8a and Waldner, A.; De Mesmaeker, A.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101-104. Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547-3552. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048-1063. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711-714. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
19. For a recent review on the use of Lewis acids in radical reaction, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562-2579. For the use of Lewis acids in radical reactions involving sulfoxides, see ref 8a and Waldner, A.; De Mesmaeker, A.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101-104. Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547-3552. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048-1063. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711-714. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
20. For a recent review on the use of Lewis acids in radical reaction, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562-2579. For the use of Lewis acids in radical reactions involving sulfoxides, see ref 8a and Waldner, A.; De Mesmaeker, A.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101-104. Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547-3552. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048-1063. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711-714. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
21. For a recent review on the use of Lewis acids in radical reaction, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562-2579. For the use of Lewis acids in radical reactions involving sulfoxides, see ref 8a and Waldner, A.; De Mesmaeker, A.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101-104. Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547-3552. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048-1063. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711-714. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
22. For a recent review on the use of Lewis acids in radical reaction, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562-2579. For the use of Lewis acids in radical reactions involving sulfoxides, see ref 8a and Waldner, A.; De Mesmaeker, A.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101-104. Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547-3552. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048-1063. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711-714. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
23. For a recent review on the use of Lewis acids in radical reaction, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562-2579. For the use of Lewis acids in radical reactions involving sulfoxides, see ref 8a and Waldner, A.; De Mesmaeker, A.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101-104. Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547-3552. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048-1063. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711-714. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
24. For a recent review on the use of Lewis acids in radical reaction, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562-2579. For the use of Lewis acids in radical reactions involving sulfoxides, see ref 8a and Waldner, A.; De Mesmaeker, A.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101-104. Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547-3552. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048-1063. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711-714. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
25. For a recent review on the use of Lewis acids in radical reaction, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562-2579. For the use of Lewis acids in radical reactions involving sulfoxides, see ref 8a and Waldner, A.; De Mesmaeker, A.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101-104. Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547-3552. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048-1063. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711-714. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
26. For a recent review on the use of Lewis acids in radical reaction, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562-2579. For the use of Lewis acids in radical reactions involving sulfoxides, see ref 8a and Waldner, A.; De Mesmaeker, A.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101-104. Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547-3552. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048-1063. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711-714. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
27. For a recent review on the use of Lewis acids in radical reaction, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2562-2579. For the use of Lewis acids in radical reactions involving sulfoxides, see ref 8a and Waldner, A.; De Mesmaeker, A.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101-104. Renaud, P.; Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803. Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547-3552. Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601-1603. Renaud, P.; Bourquard, T.; Carrupt, P.-A.; Gerster, M. Helv. Chim. Acta 1998, 81, 1048-1063. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711-714. Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794-7800.
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