Steric protection of the selenium atom of the episelenonium ion intermediate to prevent both the racemization of the chiral carbon and the selenophilic attack of carbon nucleophiles

Journal of the American Chemical Society

Volumn 118, Issue 11, 1996, Pages 2756-2757

  Toshimitsu, Akio ^a   Nakano, Katsuhiro ^a   Mukai, Takao ^a   Tamao, Kohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSELENIUM DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029931981     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9538445     Document Type: Article

References (27)

1. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
2. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
3. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
4. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
5. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
6. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
7. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
8. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
9. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
10. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
11. For recent examples, see (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. (b) Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1995, 1641. (c) Déziel, R., Malenfant, E. J. Org. Chem. 1995, 60, 4660. (d) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572. (e) Fukuzawa, S.; Kasugahara, Y.; Uemura, S. Tetrahedron Lett. 1994, 35, 9403. (f) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619. (g) Tiecco, M.; Testafern, L ; Tingoli, M.; Bagnoli, L.; Santi, C. J. Chem. Soc., Chem. Commun 1993, 637. (h) Kang, S. H.; Lee, S. B. Tetrahedron Lett. 1993, 34, 1955. (i) Mihelich, E. D.; Hite, G. A. J. Am. Chem. Soc. 1992, 114, 7318. (j) Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084. (k) Mihelich, E. D. J. Am. Chem. Soc. 1990, 112, 8995 and references cited therein
12. Toshimitsu, A.; Ito, M.; Uemura, S. J. Chem. Soc. Chem. Commun., 1989, 530. For the epimerization of the chiral ring carbon in a diastereomeric episelenonium ion intermediate, see ref 1k.
13. Alexander, R. P.; Paterson, I Tetrahedron Lett. 1983, 24, 5911. Successful examples of the carbon-carbon bond formation via the episelenonium ion intermediate have been limited to certain intramolecular reactions using olefins as a carbon nucleophile: (a) Toshimitsu, A.; Kusumoto, M.; Tanimoto, S. Bull. Inst. Chem. Res., Kyoto Univ. 1992, 70, 270. (b) Ley, S. V., Lygo, B.; Morins, H.; Morton, J. A. J. Chem. Soc., Chem. Commun. 1982, 1251. (c) Toshimitsu, A.; Uemura, S.; Okano, M. J. Chem. Soc., Chem. Commun. 1982, 87. (d) Kametani, T., Kurobe, H.; Nemoto, H. J Chem. Soc., Perkin Trans. 1 1982, 1085. and references cited therein.
14. Alexander, R. P.; Paterson, I Tetrahedron Lett. 1983, 24, 5911. Successful examples of the carbon-carbon bond formation via the episelenonium ion intermediate have been limited to certain intramolecular reactions using olefins as a carbon nucleophile: (a) Toshimitsu, A.; Kusumoto, M.; Tanimoto, S. Bull. Inst. Chem. Res., Kyoto Univ. 1992, 70, 270. (b) Ley, S. V., Lygo, B.; Morins, H.; Morton, J. A. J. Chem. Soc., Chem. Commun. 1982, 1251. (c) Toshimitsu, A.; Uemura, S.; Okano, M. J. Chem. Soc., Chem. Commun. 1982, 87. (d) Kametani, T., Kurobe, H.; Nemoto, H. J Chem. Soc., Perkin Trans. 1 1982, 1085. and references cited therein.
15. Alexander, R. P.; Paterson, I Tetrahedron Lett. 1983, 24, 5911. Successful examples of the carbon-carbon bond formation via the episelenonium ion intermediate have been limited to certain intramolecular reactions using olefins as a carbon nucleophile: (a) Toshimitsu, A.; Kusumoto, M.; Tanimoto, S. Bull. Inst. Chem. Res., Kyoto Univ. 1992, 70, 270. (b) Ley, S. V., Lygo, B.; Morins, H.; Morton, J. A. J. Chem. Soc., Chem. Commun. 1982, 1251. (c) Toshimitsu, A.; Uemura, S.; Okano, M. J. Chem. Soc., Chem. Commun. 1982, 87. (d) Kametani, T., Kurobe, H.; Nemoto, H. J Chem. Soc., Perkin Trans. 1 1982, 1085. and references cited therein.
16. Alexander, R. P.; Paterson, I Tetrahedron Lett. 1983, 24, 5911. Successful examples of the carbon-carbon bond formation via the episelenonium ion intermediate have been limited to certain intramolecular reactions using olefins as a carbon nucleophile: (a) Toshimitsu, A.; Kusumoto, M.; Tanimoto, S. Bull. Inst. Chem. Res., Kyoto Univ. 1992, 70, 270. (b) Ley, S. V., Lygo, B.; Morins, H.; Morton, J. A. J. Chem. Soc., Chem. Commun. 1982, 1251. (c) Toshimitsu, A.; Uemura, S.; Okano, M. J. Chem. Soc., Chem. Commun. 1982, 87. (d) Kametani, T., Kurobe, H.; Nemoto, H. J Chem. Soc., Perkin Trans. 1 1982, 1085. and references cited therein.
17. Alexander, R. P.; Paterson, I Tetrahedron Lett. 1983, 24, 5911. Successful examples of the carbon-carbon bond formation via the episelenonium ion intermediate have been limited to certain intramolecular reactions using olefins as a carbon nucleophile: (a) Toshimitsu, A.; Kusumoto, M.; Tanimoto, S. Bull. Inst. Chem. Res., Kyoto Univ. 1992, 70, 270. (b) Ley, S. V., Lygo, B.; Morins, H.; Morton, J. A. J. Chem. Soc., Chem. Commun. 1982, 1251. (c) Toshimitsu, A.; Uemura, S.; Okano, M. J. Chem. Soc., Chem. Commun. 1982, 87. (d) Kametani, T., Kurobe, H.; Nemoto, H. J Chem. Soc., Perkin Trans. 1 1982, 1085. and references cited therein.
18. Toshimitsu, A.; Hayashi, G ; Terao, K.; Uemura, S. J. Chem. Soc., Perkin Trans 1 1986, 343
19. 4.
20. The enantiomeric excesses of 3a - e were determined by HPLC analyses using chiral columns (Chiralcel OD (Daicel) for 3a. 3b. and 3e and Chiralpak AD (Daicel) for 3c and 3d).
21. Total yields and isomer ratios were not affected by the mode of the addition
22. The precise mechanism of this reaction has not yet been clarified.
23. Rundel, W. Chem. Ber. 1968, 101, 2956. du Mont, W. W.; Kubiniok, S.; Peters, K.; von Schnering, H.-G. Angew. Chem., Int. Ed. Engl. 1987, 26, 780.
24. Rundel, W. Chem. Ber. 1968, 101, 2956. du Mont, W. W.; Kubiniok, S.; Peters, K.; von Schnering, H.-G. Angew. Chem., Int. Ed. Engl. 1987, 26, 780.
25. Pearson, D. E.; Frazer, M. G.; Frazer, V. S.; Washburn, L C. Synthesis 1976, 621.
26. These reactions were carried out at the concentration of 0.001 mol/L using the reverse addition
27. In addition to the steric protection, an electron-withdrawing effect of the substituent(s) seems to contribute to prevent the racemization Thus, we have found that while the steric protection by the 2,6-bis(trifluoromethyl)phenyl group on the selenium group is insufficient to prevent the selenophilic attack by carbon nucleophiles, the Ritter-type reaction proceeds stereospecifically without loss of the optical purity Further study is now in progress in our laboratory to clarify the origin of the electronic effect.