The ene reaction of 3-methylene-2,3-dihydrofuran with aldehydes

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 7893-7896

  Miles, William H ^a   Berreth, Christina L ^a   Anderton, Christian A ^a  

^a LAFAYETTE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605114     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01766-2     Document Type: Article

References (28)

1. 1. Comprehensive Heterocyclic Chemistry; Bird, C. W.; Cheeseman, G. W. H., Eds.; Pergamon Press: New York, 1984; Vol. 4.
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3. 3. Miles, W. H.; Berreth, C. L.; Smiley, P. M. Tetrahedron Lett. 1993, 34, 5221.
4. 4. For reviews of the ene reaction see Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. For further examples of the ene reaction of alicyclic isomers of aromatic compounds see Maischein, J.; Vilsmaier, E. Liebigs Am. Chem. 1988, 371. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am Chem. Soc. 1991, 113, 4685. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585.
5. 4. For reviews of the ene reaction see Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. For further examples of the ene reaction of alicyclic isomers of aromatic compounds see Maischein, J.; Vilsmaier, E. Liebigs Am. Chem. 1988, 371. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am Chem. Soc. 1991, 113, 4685. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585.
6. 4. For reviews of the ene reaction see Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. For further examples of the ene reaction of alicyclic isomers of aromatic compounds see Maischein, J.; Vilsmaier, E. Liebigs Am. Chem. 1988, 371. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am Chem. Soc. 1991, 113, 4685. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585.
7. 4. For reviews of the ene reaction see Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. For further examples of the ene reaction of alicyclic isomers of aromatic compounds see Maischein, J.; Vilsmaier, E. Liebigs Am. Chem. 1988, 371. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am Chem. Soc. 1991, 113, 4685. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585.
8. 4. For reviews of the ene reaction see Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. For further examples of the ene reaction of alicyclic isomers of aromatic compounds see Maischein, J.; Vilsmaier, E. Liebigs Am. Chem. 1988, 371. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am Chem. Soc. 1991, 113, 4685. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585.
9. 4. For reviews of the ene reaction see Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021. For further examples of the ene reaction of alicyclic isomers of aromatic compounds see Maischein, J.; Vilsmaier, E. Liebigs Am. Chem. 1988, 371. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am Chem. Soc. 1991, 113, 4685. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585.
10. 5. In addition to our initial report of the ene reaction of 1 with methyl vinyl ketone, acrylonitrile and ethyl acrylate, we have found that the reaction of 1 with acrolein, maleic anhydride and vinyltriphenylphosphonium bromide gives good yields of the ene product. The isomer of 1,3-methylfuran, does not react with enophiles under these conditions or under the conditions described in this paper. Experimental details will be reported in the full paper describing the ene reactions of 1 with various enophiles.
11. 6. Miles, W. H.; Smiley, P. M. J. Org. Chem. 1996, 61, 2559.
12. -1
13. 8. Lanthanide catalysis of the hetero-Diels-Alder reaction and the ene reaction has been previously noted. Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. Deaton, M. V.; Ciufolini, M. A. Tetrahedron Lett. 1993, 34, 2409.
14. 8. Lanthanide catalysis of the hetero-Diels-Alder reaction and the ene reaction has been previously noted. Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. Deaton, M. V.; Ciufolini, M. A. Tetrahedron Lett. 1993, 34, 2409.
15. 8. Lanthanide catalysis of the hetero-Diels-Alder reaction and the ene reaction has been previously noted. Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. Ziegler, F. E.; Sobolov, S. B. J. Am. Chem. Soc. 1990, 112, 2749. Deaton, M. V.; Ciufolini, M. A. Tetrahedron Lett. 1993, 34, 2409.
16. 9. Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555. Jackson, A. C.; Goldman, B. E.; Snider, B. B. J. Org. Chem. 1984, 49, 3988.
17. 9. Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555. Jackson, A. C.; Goldman, B. E.; Snider, B. B. J. Org. Chem. 1984, 49, 3988.
18. 10. Kojima, Y.; Kato, N. Tetrahedron Lett. 1979, 4667.
19. 11. For a previous study involving the ene reaction of 2-phenylpropionaldehyde, see Cartaya-Marin, C. P.; Jackson, A. C.; Snider, B. B. J. Org. Chem. 1984, 49, 2443.
20. 12. The stereochemistry of the two diastereotopic alcohols has not been definitively determined.
21. 13. The stereochemistry was assigned by comparing the spectroscopic data of alcohol 3 to (2R,3S)-and (2R,3R)-1,2-O-isopropylidene-4-phenylbutane-1,2,3-triol. Melon, D.; Gravier-Pelletier, C.; Le Merrer, Y.; Depezay, J. C. Bull. Soc. Chim. Fr. 1992, 129, 585.
22. 14. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949.
23. 15. See also Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
24. 15. See also Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
25. 15. See also Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
26. 15. See also Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
27. 3.
28. 17. Cimino, G.; De Rosa, S.; De Stevano, S., Morrone, R.; Sodano, G. Tetrahedron 1985, 41, 1093.