An oxidative Prins cyclization methodology

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 3252-3254

  Chen, Chuanfeng ^a   Mariano, Patrick S ^a  

^a UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC AMINE;

ANALYTIC METHOD; CHEMICAL REACTION KINETICS; CYCLIZATION; ELECTROCHEMICAL ANALYSIS; NOTE; OXIDATION REDUCTION REACTION; STRUCTURE ANALYSIS;

CYCLIZATION; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOTIN COMPOUNDS; OXIDATION-REDUCTION; SILANES; STEREOISOMERISM;

EID: 0034685873     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0000832     Document Type: Note

References (36)

1. Overman, L. E.; Ricca, D. J. Comprehensive Organic Synthesis; Heathcock, C., Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 1007.
2. Snider, B. B. Comprehensive Organic Synthesis; Heathcock, C., Trost, B. M., Fleming, I., Eds.; Pergamon Press; Oxford, 1991; Vol. 2, p 527. For some recent studies, see: Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271.
3. Snider, B. B. Comprehensive Organic Synthesis; Heathcock, C., Trost, B. M., Fleming, I., Eds.; Pergamon Press; Oxford, 1991; Vol. 2, p 527. For some recent studies, see: Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271.
4. Snider, B. B. Comprehensive Organic Synthesis; Heathcock, C., Trost, B. M., Fleming, I., Eds.; Pergamon Press; Oxford, 1991; Vol. 2, p 527. For some recent studies, see: Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679. Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271.
5. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
6. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
7. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
8. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
9. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
10. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
11. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
12. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
13. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
14. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
15. For allylsilane terminations, see: (a) Fleming, I.; Pearce, A.; Snowden, R. L. J. Chem. Soc., Chem. Commun. 1976, 182. (b) Castaneda, A.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695. (c) Nishiyama, H.; Itoh, K. J. Org. Chem. 1982, 47, 2496. (d) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibya, S. Heterocycles 1987, 26, 2805. (e) Mekhalfia, A.; Marko, I.E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. (f) Mekhalfia, A.; Marko, I. E. Tetrahedron Lett. 1991, 32, 4779. (g) Sano, T.; Oriyama, T. Synlett 1997, 716. For vinylsilane terminations, see: Overman, L. E.; Blumenkopf, T. A.; Castaneda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 708, 3516. Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. Berger, D.; Overman, L. E. Synlett 1992, 811.
16. Yoshida, J.; Ishichi, Y.; Isoe, S. J. Am. Chem. Soc. 1992, 114, 7594. Yoshida, J.; Takada, K.; Ishichi, Y.; Isoe, S. J. Chem. Soc., Chem. Commun. 1994, 2361.
17. Yoshida, J.; Ishichi, Y.; Isoe, S. J. Am. Chem. Soc. 1992, 114, 7594. Yoshida, J.; Takada, K.; Ishichi, Y.; Isoe, S. J. Chem. Soc., Chem. Commun. 1994, 2361.
18. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481. Linderman, R. J.; Chen, S. Tetrahedron Lett. 1995, 36, 7799. Linderman, R. J.; Chen, S. Tetrahedron Lett. 1996, 37, 3819. Duchene, A.; Boissiere, S.; Parrain, J.-L.; Quintard, J.-P. J. Organomet. Chem. 1990, 387, 153.
19. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481. Linderman, R. J.; Chen, S. Tetrahedron Lett. 1995, 36, 7799. Linderman, R. J.; Chen, S. Tetrahedron Lett. 1996, 37, 3819. Duchene, A.; Boissiere, S.; Parrain, J.-L.; Quintard, J.-P. J. Organomet. Chem. 1990, 387, 153.
20. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481. Linderman, R. J.; Chen, S. Tetrahedron Lett. 1995, 36, 7799. Linderman, R. J.; Chen, S. Tetrahedron Lett. 1996, 37, 3819. Duchene, A.; Boissiere, S.; Parrain, J.-L.; Quintard, J.-P. J. Organomet. Chem. 1990, 387, 153.
21. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481. Linderman, R. J.; Chen, S. Tetrahedron Lett. 1995, 36, 7799. Linderman, R. J.; Chen, S. Tetrahedron Lett. 1996, 37, 3819. Duchene, A.; Boissiere, S.; Parrain, J.-L.; Quintard, J.-P. J. Organomet. Chem. 1990, 387, 153.
22. Tomooka, K.; Igarashi, T.; Nakai, T. Tetrahedron 1994, 50, 5927.
23. (a) Oxidation potentials of α-stannyl ethers are in the range of 1.1-1.2 V (ref 7b), and the reduction potential of Ce(IV) is ca. 1.7 V (ref 7c).
24. (b) Yoshida, J.; Ishichi, Y.; Nishiwaki, K.; Shiozawa, S.; Isoe, S. Tetrahedron Lett. 1992, 33, 2599.
25. (c) Nair, V.; Matthew, J.; Prabhakaran, J. Chem. Soc. Rev. 1997, 26, 127.
26. (a) Prepared by Swern oxidation of the known alcohol: Lee, T. V.; Channon, J. A.; Cregg, C.; Porter, J. R.; Roden, F. S.; Yeoh, H. T. L. Tetrahedron 1989, 45, 5877. (b) Prepared by using the procedure described in Dehmlow, E. V.; Makrandi, J. K. J. Chem. Res., Synop. 1986, 32.
27. (a) Prepared by Swern oxidation of the known alcohol: Lee, T. V.; Channon, J. A.; Cregg, C.; Porter, J. R.; Roden, F. S.; Yeoh, H. T. L. Tetrahedron 1989, 45, 5877. (b) Prepared by using the procedure described in Dehmlow, E. V.; Makrandi, J. K. J. Chem. Res., Synop. 1986, 32.
28. (a) 5: Ochiao, M.; Fujita, E.; Arimoto, M.; Yamaguchi, H. Chem. Pharm. Bull. 1983, 31, 86. (b) 6 and 7: Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckhamp, W. N. J. Org. Chem. 1985, 50, 4014.
29. (a) 5: Ochiao, M.; Fujita, E.; Arimoto, M.; Yamaguchi, H. Chem. Pharm. Bull. 1983, 31, 86. (b) 6 and 7: Hiemstra, H.; Sno, M. H. A. M.; Vijn, R. J.; Speckhamp, W. N. J. Org. Chem. 1985, 50, 4014.
30. (a) Similar arguments have been advanced to explain the stereochemistry of seven-membered ring-forming Prins cyclizations (ref 3b) and sequential Prins-Pinacol reactions (ref 10b).
31. (b) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354.
32. (a) The stereochemistry of 31, for example, is assigned as cis on the basis of the observed 5.5 Hz coupling constant for the H-2 and H-3 protons and comparisons to the reported (ref 3g) 7.0 Hz coupling in closely related cis-2-phenyl-3-vinyltetrahydrofuran. In addition, the strong preference for cis-tetrahydrofuran formation in 5-exo-Prins cyclizations has been noted ealier by Oriyama (ref 3g) and Hoffmann (ref 11b).
33. (b) Hoffmann, R. W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem. 1993, 629.
34. (a) The dioxolane moiety is retained in these processes despite the report that CAN in MeCN at 70 °C effectively deprotects cyclic acetals and ketals (ref 12b). Clearly the use of only 2.1 equiv of CTAN at 25 °C is required when another oxidatively active functionality is present.
35. (b) Ates, A.; Gautier, A.; Leroy, B.; Plancher, J.-M.; Quesnel, Y.; Marko, I. E. Tetrahedron Lett. 1999, 40, 1799.
36. The anomalous removal of the sensitive dimethylacetal in conversion of 23 to 34 likely occurs during either workup or chromatographic purification rather than under the oxidative Prins cyclization conditions.