An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem "Pincer" Diels-Alder Reaction

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4418-4427

  Lautens, Mark ^a   Fillion, Eric ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001444269     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9701593     Document Type: Article

References (109)

1. For recent reviews on the Diels-Alder reaction, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: New York, 1990. (b) Intermolecular Diels-Alder reactions: Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 315. Heterodienophile additions to dienes: Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. Heterodiene additions: Boger, D. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 451. (e) Intramolecular Diels-Alder reactions: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 513, (f) Retrograde Diels-Alder reactions: Sweger, R. W.; Czarnik, A. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 551.
2. For recent reviews on the Diels-Alder reaction, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: New York, 1990. (b) Intermolecular Diels-Alder reactions: Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 315. Heterodienophile additions to dienes: Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. Heterodiene additions: Boger, D. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 451. (e) Intramolecular Diels-Alder reactions: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 513, (f) Retrograde Diels-Alder reactions: Sweger, R. W.; Czarnik, A. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 551.
3. For recent reviews on the Diels-Alder reaction, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: New York, 1990. (b) Intermolecular Diels-Alder reactions: Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 315. Heterodienophile additions to dienes: Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. Heterodiene additions: Boger, D. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 451. (e) Intramolecular Diels-Alder reactions: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 513, (f) Retrograde Diels-Alder reactions: Sweger, R. W.; Czarnik, A. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 551.
4. For recent reviews on the Diels-Alder reaction, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: New York, 1990. (b) Intermolecular Diels-Alder reactions: Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 315. Heterodienophile additions to dienes: Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. Heterodiene additions: Boger, D. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 451. (e) Intramolecular Diels-Alder reactions: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 513, (f) Retrograde Diels-Alder reactions: Sweger, R. W.; Czarnik, A. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 551.
5. For recent reviews on the Diels-Alder reaction, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: New York, 1990. (b) Intermolecular Diels-Alder reactions: Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 315. Heterodienophile additions to dienes: Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. Heterodiene additions: Boger, D. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 451. (e) Intramolecular Diels-Alder reactions: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 513, (f) Retrograde Diels-Alder reactions: Sweger, R. W.; Czarnik, A. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 551.
6. For recent reviews on the Diels-Alder reaction, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: New York, 1990. (b) Intermolecular Diels-Alder reactions: Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 315. Heterodienophile additions to dienes: Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. Heterodiene additions: Boger, D. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 451. (e) Intramolecular Diels-Alder reactions: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 513, (f) Retrograde Diels-Alder reactions: Sweger, R. W.; Czarnik, A. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 551.
7. For a critical survey on the mechanistic aspect of Diels-Alder reactions, see: Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779.
8. For recent reviews on tandem Diels-Alder cycloadditions: (a) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (b) Winkler, J. D. Chem. Rev. 1996, 96, 137. (c) Ho, T.-L. Tandem Organic Reactions; John Wiley and Sons: New York, 1992.
9. For recent reviews on tandem Diels-Alder cycloadditions: (a) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (b) Winkler, J. D. Chem. Rev. 1996, 96, 137. (c) Ho, T.-L. Tandem Organic Reactions; John Wiley and Sons: New York, 1992.
10. For recent reviews on tandem Diels-Alder cycloadditions: (a) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137. (b) Winkler, J. D. Chem. Rev. 1996, 96, 137. (c) Ho, T.-L. Tandem Organic Reactions; John Wiley and Sons: New York, 1992.
11. (a) For a recent review on aromatic heterocycles as intermediates in synthesis, see: Shipman, M. Contemp. Org. Synth. 1995, 2, 1.
12. (b) For the synthesis of a symmetrical dioxapentacycle and its enantio-selective desymmetrization, see: Marchionni, C.; Vogel, P.; Roversi, P. Tetrahedron Lett. 1996, 37, 4149.
13. (a) For recent reviews on the ring opening of oxabicyclic systems, see: Woo, S.; Keay, B. Synthesis 1996, 669.
14. (b) Chiu, P.; Lautens, M. Topics in Current Chemistry; Springer-Verlag: Berlin, in press.
15. (c) Lautens, M. Synlett 1993, 177.
16. (d) Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532.
17. (e) Lautens, M.; Klute, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 442.
18. (a) For the first use of the terms "pincer" and "domino" Diels-Alder, see: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C.; Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845.
19. (b) Paquette, L. A.; Balogh, D. W. J. Am. Chem. Soc. 1982, 104, 774.
20. Fessner, W.-D.; Sedelmeier, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626.
21. Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1931, 490, 243.
22. (a) Tochtermann, W.; Malchow, A.; Timm, H. Chem. Ber. 1978, 111, 1233.
23. (b) Lin, C.-T.; Chou, T.-C. Synthesis 1988, 628.
24. Furan and diactivated dienophile: (a) Diels, O.; Olsen, S. J. Prakt. Chem. 1940, 156, 285. (b) Stockman, H. J. Org. Chem. 1961, 26, 2025. (c) Weis, C. D. J. Org. Chem. 1963, 28, 74. (d) Kallos, J.; Deslongchamps, P. Can. J. Chem. 1966, 44, 1239. (e) Gandhi, R. P.; Chadha, V. K. J. Chem. Soc., Chem. Commun. 1968, 552. (f) Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897. (g) Weber, G.; Menke, K.; Hopf, H. Chem. Ber. 1980, 113, 531. (h) Maier, G.; Jung, W. A. Tetrahedron Lett. 1980, 21, 3875. Maier, G.; Jung, W. A. Chem. Ber. 1982, 115, 804. (j) Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
25. Furan and diactivated dienophile: (a) Diels, O.; Olsen, S. J. Prakt. Chem. 1940, 156, 285. (b) Stockman, H. J. Org. Chem. 1961, 26, 2025. (c) Weis, C. D. J. Org. Chem. 1963, 28, 74. (d) Kallos, J.; Deslongchamps, P. Can. J. Chem. 1966, 44, 1239. (e) Gandhi, R. P.; Chadha, V. K. J. Chem. Soc., Chem. Commun. 1968, 552. (f) Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897. (g) Weber, G.; Menke, K.; Hopf, H. Chem. Ber. 1980, 113, 531. (h) Maier, G.; Jung, W. A. Tetrahedron Lett. 1980, 21, 3875. Maier, G.; Jung, W. A. Chem. Ber. 1982, 115, 804. (j) Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
26. Furan and diactivated dienophile: (a) Diels, O.; Olsen, S. J. Prakt. Chem. 1940, 156, 285. (b) Stockman, H. J. Org. Chem. 1961, 26, 2025. (c) Weis, C. D. J. Org. Chem. 1963, 28, 74. (d) Kallos, J.; Deslongchamps, P. Can. J. Chem. 1966, 44, 1239. (e) Gandhi, R. P.; Chadha, V. K. J. Chem. Soc., Chem. Commun. 1968, 552. (f) Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897. (g) Weber, G.; Menke, K.; Hopf, H. Chem. Ber. 1980, 113, 531. (h) Maier, G.; Jung, W. A. Tetrahedron Lett. 1980, 21, 3875. Maier, G.; Jung, W. A. Chem. Ber. 1982, 115, 804. (j) Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
27. Furan and diactivated dienophile: (a) Diels, O.; Olsen, S. J. Prakt. Chem. 1940, 156, 285. (b) Stockman, H. J. Org. Chem. 1961, 26, 2025. (c) Weis, C. D. J. Org. Chem. 1963, 28, 74. (d) Kallos, J.; Deslongchamps, P. Can. J. Chem. 1966, 44, 1239. (e) Gandhi, R. P.; Chadha, V. K. J. Chem. Soc., Chem. Commun. 1968, 552. (f) Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897. (g) Weber, G.; Menke, K.; Hopf, H. Chem. Ber. 1980, 113, 531. (h) Maier, G.; Jung, W. A. Tetrahedron Lett. 1980, 21, 3875. Maier, G.; Jung, W. A. Chem. Ber. 1982, 115, 804. (j) Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
28. Furan and diactivated dienophile: (a) Diels, O.; Olsen, S. J. Prakt. Chem. 1940, 156, 285. (b) Stockman, H. J. Org. Chem. 1961, 26, 2025. (c) Weis, C. D. J. Org. Chem. 1963, 28, 74. (d) Kallos, J.; Deslongchamps, P. Can. J. Chem. 1966, 44, 1239. (e) Gandhi, R. P.; Chadha, V. K. J. Chem. Soc., Chem. Commun. 1968, 552. (f) Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897. (g) Weber, G.; Menke, K.; Hopf, H. Chem. Ber. 1980, 113, 531. (h) Maier, G.; Jung, W. A. Tetrahedron Lett. 1980, 21, 3875. Maier, G.; Jung, W. A. Chem. Ber. 1982, 115, 804. (j) Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
29. Furan and diactivated dienophile: (a) Diels, O.; Olsen, S. J. Prakt. Chem. 1940, 156, 285. (b) Stockman, H. J. Org. Chem. 1961, 26, 2025. (c) Weis, C. D. J. Org. Chem. 1963, 28, 74. (d) Kallos, J.; Deslongchamps, P. Can. J. Chem. 1966, 44, 1239. (e) Gandhi, R. P.; Chadha, V. K. J. Chem. Soc., Chem. Commun. 1968, 552. (f) Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897. (g) Weber, G.; Menke, K.; Hopf, H. Chem. Ber. 1980, 113, 531. (h) Maier, G.; Jung, W. A. Tetrahedron Lett. 1980, 21, 3875. Maier, G.; Jung, W. A. Chem. Ber. 1982, 115, 804. (j) Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
30. Furan and diactivated dienophile: (a) Diels, O.; Olsen, S. J. Prakt. Chem. 1940, 156, 285. (b) Stockman, H. J. Org. Chem. 1961, 26, 2025. (c) Weis, C. D. J. Org. Chem. 1963, 28, 74. (d) Kallos, J.; Deslongchamps, P. Can. J. Chem. 1966, 44, 1239. (e) Gandhi, R. P.; Chadha, V. K. J. Chem. Soc., Chem. Commun. 1968, 552. (f) Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897. (g) Weber, G.; Menke, K.; Hopf, H. Chem. Ber. 1980, 113, 531. (h) Maier, G.; Jung, W. A. Tetrahedron Lett. 1980, 21, 3875. Maier, G.; Jung, W. A. Chem. Ber. 1982, 115, 804. (j) Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
31. Furan and diactivated dienophile: (a) Diels, O.; Olsen, S. J. Prakt. Chem. 1940, 156, 285. (b) Stockman, H. J. Org. Chem. 1961, 26, 2025. (c) Weis, C. D. J. Org. Chem. 1963, 28, 74. (d) Kallos, J.; Deslongchamps, P. Can. J. Chem. 1966, 44, 1239. (e) Gandhi, R. P.; Chadha, V. K. J. Chem. Soc., Chem. Commun. 1968, 552. (f) Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897. (g) Weber, G.; Menke, K.; Hopf, H. Chem. Ber. 1980, 113, 531. (h) Maier, G.; Jung, W. A. Tetrahedron Lett. 1980, 21, 3875. Maier, G.; Jung, W. A. Chem. Ber. 1982, 115, 804. (j) Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
32. Furan and diactivated dienophile: (a) Diels, O.; Olsen, S. J. Prakt. Chem. 1940, 156, 285. (b) Stockman, H. J. Org. Chem. 1961, 26, 2025. (c) Weis, C. D. J. Org. Chem. 1963, 28, 74. (d) Kallos, J.; Deslongchamps, P. Can. J. Chem. 1966, 44, 1239. (e) Gandhi, R. P.; Chadha, V. K. J. Chem. Soc., Chem. Commun. 1968, 552. (f) Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897. (g) Weber, G.; Menke, K.; Hopf, H. Chem. Ber. 1980, 113, 531. (h) Maier, G.; Jung, W. A. Tetrahedron Lett. 1980, 21, 3875. Maier, G.; Jung, W. A. Chem. Ber. 1982, 115, 804. (j) Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
33. Furan and diactivated dienophile: (a) Diels, O.; Olsen, S. J. Prakt. Chem. 1940, 156, 285. (b) Stockman, H. J. Org. Chem. 1961, 26, 2025. (c) Weis, C. D. J. Org. Chem. 1963, 28, 74. (d) Kallos, J.; Deslongchamps, P. Can. J. Chem. 1966, 44, 1239. (e) Gandhi, R. P.; Chadha, V. K. J. Chem. Soc., Chem. Commun. 1968, 552. (f) Slee, J. D.; LeGoff, E. J. Org. Chem. 1970, 35, 3897. (g) Weber, G.; Menke, K.; Hopf, H. Chem. Ber. 1980, 113, 531. (h) Maier, G.; Jung, W. A. Tetrahedron Lett. 1980, 21, 3875. Maier, G.; Jung, W. A. Chem. Ber. 1982, 115, 804. (j) Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
34. Furan and monoactivated dienophile: (a) Gelin, R.; Debard, A. Bull. Soc. Chim. Fr. 1966, 144. (b) McCulloch, A. W.; Smith, D. G.; McInnes, A. G. Can. J. Chem. 1974, 52, 1013. (c) McCulloch, A. W.; McInnes, A. G. Can. J. Chem. 1975, 53, 1496. For an example of a regioselective Diels-Alder reaction of 2-methylfuran with an unsymmetrical deactivated acetylenic dienophile, see: Gorgues, A.; Simon, A.; Le Coq, A.; Hercouet, A.; Corre, F. Tetrahedron 1986, 42, 351. (e) Lasne, M.-C.; Ripoll, J.-L. Bull. Soc. Chim. Fr. 1986, 766.
35. Furan and monoactivated dienophile: (a) Gelin, R.; Debard, A. Bull. Soc. Chim. Fr. 1966, 144. (b) McCulloch, A. W.; Smith, D. G.; McInnes, A. G. Can. J. Chem. 1974, 52, 1013. (c) McCulloch, A. W.; McInnes, A. G. Can. J. Chem. 1975, 53, 1496. For an example of a regioselective Diels-Alder reaction of 2-methylfuran with an unsymmetrical deactivated acetylenic dienophile, see: Gorgues, A.; Simon, A.; Le Coq, A.; Hercouet, A.; Corre, F. Tetrahedron 1986, 42, 351. (e) Lasne, M.-C.; Ripoll, J.-L. Bull. Soc. Chim. Fr. 1986, 766.
36. Furan and monoactivated dienophile: (a) Gelin, R.; Debard, A. Bull. Soc. Chim. Fr. 1966, 144. (b) McCulloch, A. W.; Smith, D. G.; McInnes, A. G. Can. J. Chem. 1974, 52, 1013. (c) McCulloch, A. W.; McInnes, A. G. Can. J. Chem. 1975, 53, 1496. For an example of a regioselective Diels-Alder reaction of 2-methylfuran with an unsymmetrical deactivated acetylenic dienophile, see: Gorgues, A.; Simon, A.; Le Coq, A.; Hercouet, A.; Corre, F. Tetrahedron 1986, 42, 351. (e) Lasne, M.-C.; Ripoll, J.-L. Bull. Soc. Chim. Fr. 1986, 766.
37. Furan and monoactivated dienophile: (a) Gelin, R.; Debard, A. Bull. Soc. Chim. Fr. 1966, 144. (b) McCulloch, A. W.; Smith, D. G.; McInnes, A. G. Can. J. Chem. 1974, 52, 1013. (c) McCulloch, A. W.; McInnes, A. G. Can. J. Chem. 1975, 53, 1496. For an example of a regioselective Diels-Alder reaction of 2-methylfuran with an unsymmetrical deactivated acetylenic dienophile, see: Gorgues, A.; Simon, A.; Le Coq, A.; Hercouet, A.; Corre, F. Tetrahedron 1986, 42, 351. (e) Lasne, M.-C.; Ripoll, J.-L. Bull. Soc. Chim. Fr. 1986, 766.
38. Furan and monoactivated dienophile: (a) Gelin, R.; Debard, A. Bull. Soc. Chim. Fr. 1966, 144. (b) McCulloch, A. W.; Smith, D. G.; McInnes, A. G. Can. J. Chem. 1974, 52, 1013. (c) McCulloch, A. W.; McInnes, A. G. Can. J. Chem. 1975, 53, 1496. For an example of a regioselective Diels-Alder reaction of 2-methylfuran with an unsymmetrical deactivated acetylenic dienophile, see: Gorgues, A.; Simon, A.; Le Coq, A.; Hercouet, A.; Corre, F. Tetrahedron 1986, 42, 351. (e) Lasne, M.-C.; Ripoll, J.-L. Bull. Soc. Chim. Fr. 1986, 766.
39. (a) Berson, J. A. J. Am. Chem. Soc. 1953, 75, 1240.
40. (b) Sasaki, T.; Kanematsu, K.; Iizuka, K. Heterocycles 1975, 3, 109.
41. (a) Kapicak, L. A.; Battiste, M. A. J. Chem. Soc., Chem. Commun. 1973, 930.
42. (b) Hall, R. H.; Harkema, S.; den Hertog, H. J.; van Hummel, G. J.; Reinhoudt, D. N. Rev. Trav. Chim. Pays-Bas 1981, 100, 312.
43. (c) Halverson, A.; Keehn, P. M. J. Am. Chem. Soc. 1982, 104, 6125.
44. (d) Wollenweber, M.; Fritz, H.; Rihs, G.; Prinzbach, H. Chem. Ber. 1991, 124, 2465.
45. (a) For a detailed study on the Diels-Alder reaction between furan and dimethyl acetylenedicarboxylate, see: McCulloch, A. W.; Smith, D. G.; McInnes, A. G. Can, J. Chem. 1973, 51, 4125.
46. (b) An explanation of the stereoselective cycloaddition of furan with oxanorbornadienomaleimide and oxanorbornadiene anhydride intermediates based on semiempirical molecular orbital calculations has been reported; see: Warrener, R. N.; Elsey, G. M.; Maksimovic, L.; Johnston, M. R.; Kennard, C. H. L. Tetrahedron Lett. 1995, 42, 7753.
47. Jurczak, J.; Belniak, S.; Kozluk, T.; Pikul, S.; Salanski, P. Bull. Pol. Acad. Sci., Chem. 1984, 32, 135.
48. (a) Iten, P. X.; Eugster, C. H. Helv. Chim. Acta 1978, 61, 1134.
49. (b) Smith, J. G.; Dibble, P. W.; Sandborn, R. E. J. Org. Chem. 1986, 57, 3762.
50. (c) Suzuki, T.; Kubomura, K.; Fuchii, H.; Takayama H. J. Chem. Soc., Chem. Commun. 1990, 1687.
51. (d) Suzuki, T.; Kubomura, K.; Fuchii, H.; Takayama, H. J. Chem. Soc., Chem. Commun. 1991, 204.
52. (e) Suzuki, T.; Kubomura, K.; Takayama, H. Heterocycles 1994, 38, 961.
53. (f) Takeshita, H.; Mori, A.; Kato, N.; Kurahashi, Y.; Ito, M. Bull. Chem. Soc. Jpn. 1995, 68, 2669.
54. (a) Russell, R. A.; Longmore, R. W.; Weerasuria, K. D. V.; Warrener, R. N. Aust. J. Chem. 1991, 44, 1341.
55. (b) Nezis, A.; Fayn, J.; Cambon, A. J. Fluorine Chem. 1991, 53, 285.
56. (c) Barlow, M. G.; Tajammal, S.; Tipping, A. E. J. Fluorine Chem. 1993, 62, 95.
57. (d) Barlow, M. G.; Pritchard, R. G.; Tajammal, S.; Tipping, A. E. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1993, C49, 2151.
58. (e) Barlow, M. G.; Suliman, N. N. E.; Tipping, A. E. J. Fluorine Chem. 1995, 70, 59.
59. (f) Barlow, M. G.; Suliman, N. N. E.; Tipping, A. E. J. Fluorine Chem. 1995, 70, 95.
60. (g) Barlow, M. G.; Suliman, N. N. E.; Tipping, A. E. J. Fluorine Chem. 1995, 70, 109.
61. Lautens, M.; Fillion, E. J. Org. Chem. 1996, 61, 7994.
62. Slee and LeGoff reported a 15:1 ratio of exo-endo vs exo-exo, which was shown to be erroneous by McInnis and co-workers (ref 14a). We observed a 3:1 ratio in accordance with the results of McInnis.
63. (a) For an example of "pincer" Diels-Alder using a tethered bis-pyrrole see: Visnick, M.; Battiste, M. A. J. Chem. Soc., Chem. Commun. 1985, 1621.
64. (b) The exo addition of furan on the oxanorbornadiene intermediate, yielding predominantly the exo-endo adduct, was explained by Slee and LeGoff in terms of the bulk of the methyl esters (ref 10f).
65. (a) Cram, D. J.; Knox, G. R. J. Am. Chem. Soc. 1961, 83, 2204.
66. (b) Gram, D. J.; Montgomery, C. S.; Knox, G. R. J. Am. Chem. Soc. 1986, 88, 515.
67. Some authors refer to this stereochemistry as endo-endo (refs 10a,b,e, 11b, and 14a).
68. Stockman was the first to perform this experiment (ref 10b) but incorrectly assigned the stereochemistry as exo-endo.
69. (a) Warrener, R. N.; Butler, D. N.; Liao, W. Y.; Pitt, I. G.; Russell, R. A. Tetrahedron Lett. 1991, 32, 1889,
70. (b) Warrener, R. N.; Maksimovic, L. Tetrahedron Lett. 1994, 35, 2389.
71. (c) Warrener, R. N.; Maksimovic, L.; Butler, D. N. J. Chem. Soc., Chem. Commun. 1994, 1831.
72. (d) Warrener, R. N.; Wang, S.; Maksimovic, L.; Tepperman, P. M.; Butler, D. N. Tetrahedron Lett. 1995, 36, 6141.
73. (e) Warrener, R. N.; Maksimovic, L.; Pitt, I. G.; Mahadevan, I.; Russell, R. A.; Tiekink, E. R. T. Tetrahedron Lett. 1996, 36, 3773.
74. Pollmann, M.; Müllen, K. J. Am. Chem. Soc. 1994, 116, 2318.
75. (a) Luo, J.; Hart, H. J. Org. Chem. 1988, 53, 1343.
76. (b) Blatter, K.; Godt, A.; Vogel, T.; Schlüter, A.-D. Makromol. Chem. Macromol. Symp. 1991, 44, 265.
77. (c) Packe, R.; Enkelmann, V.; Schlüter, A.-D. Makromol. Chem. 1992, 193, 2829.
78. (d) Schürmann, B. L.; Enkelmann, V.; Löffler, M.; Schlüter, A.-D. Angew. Chem., Int. Ed. Engl. 1993, 32, 123.
79. (a) Kitzing, R.; Fuchs, R.; Joyeux, M.; Prinzbach, H. Helv. Chim. Acta 1968, 51, 888.
80. (b) Bansal, R. C.; McCulloch, A. W.; McInnes, A. G. Can. J. Chem. 1969, 47, 2391.
81. (c) Bansal, R. C.; McCulloch, A. W.; McInnes, A. G. Can. J. Chem. 1970, 48, 1472.
82. (d) For a recent review on the synthesis of azabicyclic systems see: Chen, Z.; Trudell, M. L. Chem. Rev, 1996, 96, 1179.
83. (a) McCulloch, A. W.; Stanovnik, B.; Smith, D. G.; McInnes, A. G. Can J. Chem. 1969, 47, 4319.
84. (b) Anderson, W. K.; Dewey, R. H. J. Med. Chem. 1977, 20, 306.
85. (c) Xing, Y. D.; Huang, N. Z. J. Org. Chem. 1982, 47, 140.
86. (d) For the asymmetric synthesis of oxanorbornadiene intermediates see: Sha, C.-K.; Shen, C.-Y.; Lee, R.-S.; Lee, S.-R.; Wang, S.-L. Tetrahedron Lett. 1995, 36, 1283.
87. Wenkert, E.; Quo, M.; Lavilla, R.; Porter, B.; Ramachandran, K.; Sheu, J.-H. J. Org. Chem. 1990, 55, 6203.
88. Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929.
89. Zanetti, J. E. J. Am. Chem. Soc. 1927, 49, 1065.
90. Zanetti, J. E.; Beckmann, C. O. J. Am. Chem. Soc. 1928, 50, 2031.
91. Zambias, R. A.; Caldwell, C. G.; Kopka, I. E.; Hammond, M. L. J. Org. Chem. 1988, 53, 4135.
92. (a) Nystrom, R. F.; Berger, C. R. A. J. Am. Chem. Soc. 1958, 80, 2896.
93. (b) Scharf, H.-D.; Wolters, E. Chem. Ber. 1978, 111, 639.
94. (c) Buxton, S. R.; Holm, K. H.; Skattebøl, L. Tetrahedron Lett. 1987, 28, 2167.
95. Shen, M.; Schultz, A. G. Tetrahedron Lett. 1981, 22, 3347.
96. Jones, E. R. H.; Shen, T. Y.; Whiting, M. C. J. Chem. Soc. 1950, 236.
97. Larock, R. C.; Liu, C.-L. J. Org. Chem. 1983, 48, 2151.
98. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
99. Papadopoulos, E. P.; Haidar, N. F. Tetrahedron Lett. 1968, 9, 1721.
100. Hasan, I.; Marinelli, E. R.; Chang Lin, L.-C.; Fowler, F. W.; Levy, A. B. J. Org. Chem. 1981, 46, 157.
101. (a) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595.
102. (b) Forman, M. A.; Dailey, W. P. J. Am. Chem. Soc. 1991, 113, 2761.
103. Heard, N. E.; Turner J. J. Org. Chem. 1995, 60, 4302.
104. For the synthesis of an azaoxabicyclic system from the reaction of furo[2,3-c]pyrroles with 2 equiv of DMAD, see: Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193.
105. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystal-lographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
106. A similar observation has been noted by Danishefsky in his work with β-(phenylsulfinyl)-α,β-unsaturated carbonyl dienophiles. Danishefsky, S.; Harayama, T. J.; Singh, R. K. J. Am. Chem. Soc. 1979, 101, 7008.
107. (a) Commercially available.
108. (b) Truce, W. E.; Onken, D. W. J. Org. Chem. 1975, 40, 3200.
109. For the synthesis of 2,2′-bifuryl-DMAD adducts, see: Grigg, R.; Roffey, P.; Sargent, M. V. J. Chem. Soc. C 1967, 2327.