Palladium-catalyzed reaction of propargyl nucleophiles with α-sulfonyl α,β-unsaturated ketones: A single-step synthesis of furo[3,4-c] heterocyclic derivatives

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 3223-3226

  Monteiro, Nuno ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; KETONE; PALLADIUM;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON TRANSPORT; NOTE; REACTION ANALYSIS;

EID: 0034685919     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991817h     Document Type: Note

References (35)

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18. Palladium-mediated reactions in which the intermediacy of a catalytic palladium carbene has been suggested are scarce. See: Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196. Trost, B. M.; Schneider, S. J. Am. Chem. Soc. 1989, 111, 4430. Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. Busacca, C. A.; Swestock, J.; Johnson, R. E.; Bailey, T. R.; Musza, L.; Rodger, C. A. J. Org. Chem. 1994, 59, 7553. Farina, V.; Hossain, M. A. Tetrahedron Lett. 1996, 37, 6997. Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295. Schweizer, S.; Song, Z.-Z.; Meyer, F. E.; Parsons, P. J.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1452. Sierra, M. A.; Manchen̄o, M. J.; Saez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812.
19. Palladium-mediated reactions in which the intermediacy of a catalytic palladium carbene has been suggested are scarce. See: Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196. Trost, B. M.; Schneider, S. J. Am. Chem. Soc. 1989, 111, 4430. Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. Busacca, C. A.; Swestock, J.; Johnson, R. E.; Bailey, T. R.; Musza, L.; Rodger, C. A. J. Org. Chem. 1994, 59, 7553. Farina, V.; Hossain, M. A. Tetrahedron Lett. 1996, 37, 6997. Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295. Schweizer, S.; Song, Z.-Z.; Meyer, F. E.; Parsons, P. J.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1452. Sierra, M. A.; Manchen̄o, M. J.; Saez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812.
20. Palladium-mediated reactions in which the intermediacy of a catalytic palladium carbene has been suggested are scarce. See: Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196. Trost, B. M.; Schneider, S. J. Am. Chem. Soc. 1989, 111, 4430. Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. Busacca, C. A.; Swestock, J.; Johnson, R. E.; Bailey, T. R.; Musza, L.; Rodger, C. A. J. Org. Chem. 1994, 59, 7553. Farina, V.; Hossain, M. A. Tetrahedron Lett. 1996, 37, 6997. Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295. Schweizer, S.; Song, Z.-Z.; Meyer, F. E.; Parsons, P. J.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1452. Sierra, M. A.; Manchen̄o, M. J.; Saez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812.
21. Palladium-mediated reactions in which the intermediacy of a catalytic palladium carbene has been suggested are scarce. See: Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196. Trost, B. M.; Schneider, S. J. Am. Chem. Soc. 1989, 111, 4430. Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. Busacca, C. A.; Swestock, J.; Johnson, R. E.; Bailey, T. R.; Musza, L.; Rodger, C. A. J. Org. Chem. 1994, 59, 7553. Farina, V.; Hossain, M. A. Tetrahedron Lett. 1996, 37, 6997. Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295. Schweizer, S.; Song, Z.-Z.; Meyer, F. E.; Parsons, P. J.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1452. Sierra, M. A.; Manchen̄o, M. J.; Saez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812.
22. Palladium-mediated reactions in which the intermediacy of a catalytic palladium carbene has been suggested are scarce. See: Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196. Trost, B. M.; Schneider, S. J. Am. Chem. Soc. 1989, 111, 4430. Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. Busacca, C. A.; Swestock, J.; Johnson, R. E.; Bailey, T. R.; Musza, L.; Rodger, C. A. J. Org. Chem. 1994, 59, 7553. Farina, V.; Hossain, M. A. Tetrahedron Lett. 1996, 37, 6997. Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295. Schweizer, S.; Song, Z.-Z.; Meyer, F. E.; Parsons, P. J.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1452. Sierra, M. A.; Manchen̄o, M. J.; Saez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812.
23. Palladium-mediated reactions in which the intermediacy of a catalytic palladium carbene has been suggested are scarce. See: Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196. Trost, B. M.; Schneider, S. J. Am. Chem. Soc. 1989, 111, 4430. Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. Busacca, C. A.; Swestock, J.; Johnson, R. E.; Bailey, T. R.; Musza, L.; Rodger, C. A. J. Org. Chem. 1994, 59, 7553. Farina, V.; Hossain, M. A. Tetrahedron Lett. 1996, 37, 6997. Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295. Schweizer, S.; Song, Z.-Z.; Meyer, F. E.; Parsons, P. J.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1452. Sierra, M. A.; Manchen̄o, M. J.; Saez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812.
24. Palladium-mediated reactions in which the intermediacy of a catalytic palladium carbene has been suggested are scarce. See: Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196. Trost, B. M.; Schneider, S. J. Am. Chem. Soc. 1989, 111, 4430. Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. Busacca, C. A.; Swestock, J.; Johnson, R. E.; Bailey, T. R.; Musza, L.; Rodger, C. A. J. Org. Chem. 1994, 59, 7553. Farina, V.; Hossain, M. A. Tetrahedron Lett. 1996, 37, 6997. Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295. Schweizer, S.; Song, Z.-Z.; Meyer, F. E.; Parsons, P. J.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1452. Sierra, M. A.; Manchen̄o, M. J.; Saez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812.
25. Palladium-mediated reactions in which the intermediacy of a catalytic palladium carbene has been suggested are scarce. See: Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196. Trost, B. M.; Schneider, S. J. Am. Chem. Soc. 1989, 111, 4430. Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. Busacca, C. A.; Swestock, J.; Johnson, R. E.; Bailey, T. R.; Musza, L.; Rodger, C. A. J. Org. Chem. 1994, 59, 7553. Farina, V.; Hossain, M. A. Tetrahedron Lett. 1996, 37, 6997. Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295. Schweizer, S.; Song, Z.-Z.; Meyer, F. E.; Parsons, P. J.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1452. Sierra, M. A.; Manchen̄o, M. J.; Saez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812.
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30. For a recent review on the synthesis of furans, see: Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955.
31. Ye, X.-S.; Yu, P.; Wong, H. N. C. Liebiegs Ann./Recl. 1997, 459.
32. Analogous furans have previously been synthesized by metal-mediated reactions of diazo compounds: Wee, A. G. H.; Liu, B.; Zhang, L. J. Org. Chem. 1992, 57, 4404. Padwa, A; Kinder, F. R. J. Org. Chem. 1993, 58, 21. Gettwert, V.; Krebs, F.; Maas, G. Eur. J. Org. Chem. 1999, 1213, 3. See also ref 4.
33. Analogous furans have previously been synthesized by metal- mediated reactions of diazo compounds: Wee, A. G. H.; Liu, B.; Zhang, L. J. Org. Chem. 1992, 57, 4404. Padwa, A; Kinder, F. R. J. Org. Chem. 1993, 58, 21. Gettwert, V.; Krebs, F.; Maas, G. Eur. J. Org. Chem. 1999, 1213, 3. See also ref 4.
34. Analogous furans have previously been synthesized by metal- mediated reactions of diazo compounds: Wee, A. G. H.; Liu, B.; Zhang, L. J. Org. Chem. 1992, 57, 4404. Padwa, A; Kinder, F. R. J. Org. Chem. 1993, 58, 21. Gettwert, V.; Krebs, F.; Maas, G. Eur. J. Org. Chem. 1999, 1213, 3. See also ref 4.
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