One-Step Synthesis and Highly Regio- and Stereoselective Diels-Alder Cycloadditions of Novel exo-2-Oxazolidinone Dienes

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 4105-4115

  Mandal, Ashis B ^a   Gómez, Adriana ^a   Trujillo, Gonzalo ^a   Méndez, Francisco ^b   Jiménez, Hugo A ^a   De Rosales, Maria Jesús ^c   Martínez, Rafael ^a   Delgado, Francisco ^a   Tamariz, Joaquín ^a  

^a INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

^b UNIVERSIDAD AUTÓNOMA METROPOLITANA   (Mexico)

^c DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000378694     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962403g     Document Type: Article

References (48)

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8. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
9. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
10. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
11. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
12. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
13. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
14. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
15. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
16. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
17. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
18. For recent examples: (a) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (b) Sha, C.-K.; Lee, R.-S.; Wang, Y. Tetrahedron 1995, 51, 193. (c) Van der Baan, J. L.; van der Heide, T. A. J.; van der Louw, J.; Klumpp, G. W. Synlett 1995, 1. (d) Leung, M.-k.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841. (e) Chou, C.-H.; Trahanovsky, W. S. J. Org. Chem. 1995, 60, 5449. (f) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc., Chem. Commun. 1995, 2537. (g) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1735. (h) White, L. A.; Storr, R. C. Tetrahedron 1996, 52, 3117. (i) Tso, H.-H.; Chang, Y.-M.; Tsay, H. Synth. Commun. 1996, 26, 569. (j) Tso, H.-H.; Chandrasekharam, M. Tetrahedron Lett. 1996, 37, 4189. (k) Carly, P. R.; Cappelle, S. L.; Campernolle, F.; Hoornaert, G. J. Tetrahedron 1996, 52, 11889. (l) Chou, T.-s.; Wang, C.-T. Tetrahedron 1996, 52, 12459. (m) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166, and references cited therein.
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48. See Scheme 1 for the numbering scheme used.