Palladium-Catalyzed Allylic Substitution in γ-Oxygenated Vinyl Sulfones: One-Step Synthesis of Tetrasubstituted Dihydrofurans

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5682-5683

  Alonso, Inés ^a   Carretero, Juan C ^a   Garrido, Jose L ^a   Magro, Virginia ^a   Pedregal, Concepción ^a,b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001381169     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970864b     Document Type: Article

References (31)

1. For some recent reviews, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995; p 290-422.
2. For some recent reviews, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995; p 290-422.
3. For some recent reviews, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Williams, J. M. J. Synlett 1996, 705. (c) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995; p 290-422.
4. For palladium-catalyzed allylic substitutions in γ-oxygenated-α,β-unsaturated esters, see: (a) Tanikaga, R.; Jun, T. X.; Kaji, A. J. Chem. Soc., Perkin Trans. 1 1990, 1185. (b) Tsuda, T.; Horii, Y.; Nakagawa, Y.; Ishida, T.; Saegusa, T. J. Org. Chem. 1989, 54, 977. (c) Tanikaga, R.; Takeuchi, J.; Takyu, M.; Kaji, A. J. Chem. Soc., Chem. Commun. 1987, 386. (d) Tsuji, J.; Ueno, H.; Kobayashi, Y.; Okumoto, H. Tetrahedron Lett. 1981, 22, 2573.
5. For palladium-catalyzed allylic substitutions in γ-oxygenated-α,β-unsaturated esters, see: (a) Tanikaga, R.; Jun, T. X.; Kaji, A. J. Chem. Soc., Perkin Trans. 1 1990, 1185. (b) Tsuda, T.; Horii, Y.; Nakagawa, Y.; Ishida, T.; Saegusa, T. J. Org. Chem. 1989, 54, 977. (c) Tanikaga, R.; Takeuchi, J.; Takyu, M.; Kaji, A. J. Chem. Soc., Chem. Commun. 1987, 386. (d) Tsuji, J.; Ueno, H.; Kobayashi, Y.; Okumoto, H. Tetrahedron Lett. 1981, 22, 2573.
6. For palladium-catalyzed allylic substitutions in γ-oxygenated-α,β-unsaturated esters, see: (a) Tanikaga, R.; Jun, T. X.; Kaji, A. J. Chem. Soc., Perkin Trans. 1 1990, 1185. (b) Tsuda, T.; Horii, Y.; Nakagawa, Y.; Ishida, T.; Saegusa, T. J. Org. Chem. 1989, 54, 977. (c) Tanikaga, R.; Takeuchi, J.; Takyu, M.; Kaji, A. J. Chem. Soc., Chem. Commun. 1987, 386. (d) Tsuji, J.; Ueno, H.; Kobayashi, Y.; Okumoto, H. Tetrahedron Lett. 1981, 22, 2573.
7. For palladium-catalyzed allylic substitutions in γ-oxygenated-α,β-unsaturated esters, see: (a) Tanikaga, R.; Jun, T. X.; Kaji, A. J. Chem. Soc., Perkin Trans. 1 1990, 1185. (b) Tsuda, T.; Horii, Y.; Nakagawa, Y.; Ishida, T.; Saegusa, T. J. Org. Chem. 1989, 54, 977. (c) Tanikaga, R.; Takeuchi, J.; Takyu, M.; Kaji, A. J. Chem. Soc., Chem. Commun. 1987, 386. (d) Tsuji, J.; Ueno, H.; Kobayashi, Y.; Okumoto, H. Tetrahedron Lett. 1981, 22, 2573.
8. (a) Adrio, J.; Carretero, J. C.; Gómez Arrayás, R. Synlett 1996, 640.
9. (b) Carretero, J. C.; Gómez Arrayás, R.; Storch, I. Tetrahedron Lett. 1996, 37, 3379.
10. (c) Carretero, J. C.; Gómez Arrayás, R. J. Org. Chem. 1995, 60, 6000.
11. (d) De Blas, J.; Carretero, J. C.; Domínguez, E. Tetrahedron Lett. 1994, 35, 4603.
12. (e) Domínguez, E.; Carretero, J. C. Tetrahedron 1994, 50, 7557.
13. (a) Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949.
14. (b) Enders, D.; Von Berg, S.; Jandeleit, B. Synlett 1996, 18.
15. (a) Domínguez, E.; Carretero, J. C. Tetrahedron 1990, 46, 7197.
16. (b) Trost, B. M.; Grese, T. A. J. Org. Chem. 1991, 56, 3189.
17. 3 were used as ligands.
18. (a) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523.
19. (b) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y. Tetrahedron Lett. 1982, 23, 4809.
20. 3, dppp, dppf and neocuproine were also tested, the best yields were obtained in the presence of dppe.
21. A significant decrease in the yields of the γ-substituted products was observed when the reactions were performed in the absence of molecular sieves due to the competitive hydrolysis of the carbonates 2 to the corresponding alcohols 1.
22. For other recent synthesis of dihydrofurans based on tandem processes, see: (a) Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. (b) Hagiwara, H.; Sato, K.; Suzuki, T.; Ando, M, Tetrahedron Lett. 1997, 38, 2103. Hayashi, T.; Yamane, M.; Ohno, A. J. Org. Chem. 1997, 62, 204. Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221.
23. For other recent synthesis of dihydrofurans based on tandem processes, see: (a) Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. (b) Hagiwara, H.; Sato, K.; Suzuki, T.; Ando, M, Tetrahedron Lett. 1997, 38, 2103. Hayashi, T.; Yamane, M.; Ohno, A. J. Org. Chem. 1997, 62, 204. Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221.
24. For other recent synthesis of dihydrofurans based on tandem processes, see: (a) Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. (b) Hagiwara, H.; Sato, K.; Suzuki, T.; Ando, M, Tetrahedron Lett. 1997, 38, 2103. Hayashi, T.; Yamane, M.; Ohno, A. J. Org. Chem. 1997, 62, 204. Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221.
25. For other recent synthesis of dihydrofurans based on tandem processes, see: (a) Lee, Y. R.; Kim, B. S. Tetrahedron Lett. 1997, 38, 2095. (b) Hagiwara, H.; Sato, K.; Suzuki, T.; Ando, M, Tetrahedron Lett. 1997, 38, 2103. Hayashi, T.; Yamane, M.; Ohno, A. J. Org. Chem. 1997, 62, 204. Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221.
26. Substrate 2c reacted to give a mixture of products, predominating the formation of 4-methyl-1-benzenesulfonyl-1,3-pentadiene (24-37% yield) likely due to the competitive β-elimination process on the π-allylpalladium intermediate.
27. 3). Equation Presented
28. 3 in this cyclization step may be due to its reversible coordination with the double bond, thus activating the conjugate addition of either the phosphine or the formed enolate. For metal-promoted Michael reactions requiring the presence of free phosphine, see: Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553 (and references cited therein).
29. For some recent phosphine-catalyzed nucleophile additions, see: (a) Zhang, C.; Lu, X. Synlett 1995, 645. (b) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819.
30. For some recent phosphine-catalyzed nucleophile additions, see: (a) Zhang, C.; Lu, X. Synlett 1995, 645. (b) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819.
31. Carretero, J. C.; Domínguez, E. J. Org. Chem. 1992, 57, 3867.