Lewis Acid-Catalyzed Ring-Opening Reactions of Semicyclic N,O-Acetals

Organic Letters

Volumn 3, Issue 3, 2001, Pages 477-480

  Sugiura, Masaharu ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

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ARTICLE;

EID: 0000094470     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006990a     Document Type: Article

References (22)

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2. Gabbutt, C. D.; Hepworth, J. D. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Kirby, G. W., Volume Ed.; Pergamon: Oxford, 1995; Vol. 4, pp 293-349.
3. For reviews, see: (a) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 1047-1082. (b) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
4. For reviews, see: (a) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 1047-1082. (b) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
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11. Okitsu, O.; Suzuki, R.; Kobayashi, S. Synlett 2000, 989.
12. Related reactions of benzamides have been reported: Chen, J.; Crooks, P. A.; Hussain, A. Int. J. Pharm. 1995, 123, 95.
13. For a leading reference: Mukaiyama, T.; Takashima, T.; Katsurada, M.; Aizawa, H. Chem. Lett. 1991, 533.
14. 1H NMR spectra of 11 and 6a are quite similar, the chemical shifts for the methylene proton adjacent to the silyloxy group or the hydroxyl group are distinguishable, i.e., 3.55 ppm (t) for 11 and 3.60 ppm (t) for 6a.
15. Nagai et al. suggested a similar transition state model for α-alkoxy-N,N-dibenzyliminium ion system (see. ref 4a).
16. For recent syntheses of isofebrifugine and/or febrifugine, see: (a) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255. (b) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175. (c) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.-S.; Wataya, Y. J. Org. Chem. 1999, 64, 6833. (d) Takeuchi, Y.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 905. (e) Takeuchi, Y.; Hattori, M.; Abe, H.; Harayama, T. Synthesis 1999, 1814. (f) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Harayama, T. Chem. Commun. 2000, 1643. (g) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.
17. For recent syntheses of isofebrifugine and/or febrifugine, see: (a) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255. (b) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175. (c) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.-S.; Wataya, Y. J. Org. Chem. 1999, 64, 6833. (d) Takeuchi, Y.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 905. (e) Takeuchi, Y.; Hattori, M.; Abe, H.; Harayama, T. Synthesis 1999, 1814. (f) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Harayama, T. Chem. Commun. 2000, 1643. (g) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.
18. For recent syntheses of isofebrifugine and/or febrifugine, see: (a) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255. (b) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175. (c) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.-S.; Wataya, Y. J. Org. Chem. 1999, 64, 6833. (d) Takeuchi, Y.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 905. (e) Takeuchi, Y.; Hattori, M.; Abe, H.; Harayama, T. Synthesis 1999, 1814. (f) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Harayama, T. Chem. Commun. 2000, 1643. (g) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.
19. For recent syntheses of isofebrifugine and/or febrifugine, see: (a) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255. (b) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175. (c) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.-S.; Wataya, Y. J. Org. Chem. 1999, 64, 6833. (d) Takeuchi, Y.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 905. (e) Takeuchi, Y.; Hattori, M.; Abe, H.; Harayama, T. Synthesis 1999, 1814. (f) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Harayama, T. Chem. Commun. 2000, 1643. (g) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.
20. For recent syntheses of isofebrifugine and/or febrifugine, see: (a) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255. (b) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175. (c) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.-S.; Wataya, Y. J. Org. Chem. 1999, 64, 6833. (d) Takeuchi, Y.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 905. (e) Takeuchi, Y.; Hattori, M.; Abe, H.; Harayama, T. Synthesis 1999, 1814. (f) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Harayama, T. Chem. Commun. 2000, 1643. (g) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.
21. For recent syntheses of isofebrifugine and/or febrifugine, see: (a) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255. (b) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175. (c) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.-S.; Wataya, Y. J. Org. Chem. 1999, 64, 6833. (d) Takeuchi, Y.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 905. (e) Takeuchi, Y.; Hattori, M.; Abe, H.; Harayama, T. Synthesis 1999, 1814. (f) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Harayama, T. Chem. Commun. 2000, 1643. (g) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.
22. For recent syntheses of isofebrifugine and/or febrifugine, see: (a) Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255. (b) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175. (c) Kobayashi, S; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.-S.; Wataya, Y. J. Org. Chem. 1999, 64, 6833. (d) Takeuchi, Y.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 1999, 47, 905. (e) Takeuchi, Y.; Hattori, M.; Abe, H.; Harayama, T. Synthesis 1999, 1814. (f) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Harayama, T. Chem. Commun. 2000, 1643. (g) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.