Enantioselective ring-cleavage reaction of 2-substituted 1,3-dioxolanes catalyzed by arylboron complexes derived from N-Tosyl-(αS,βR)-β-methyltryptophan

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 6772-6773

  Kinugasa, Motoharu ^a   Harada, Toshiro ^a   Oku, Akira ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001361182     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961498j     Document Type: Article

References (40)

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3. For enantioselective ring-cleavage of epoxides, see: (a) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643. (b) Joshi, N. N.; Srebnik, M.; Brown, H. C. J. Am. Chem. Soc. 1988, 110, 6246. (c) Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213. (d) Hayashi, M.; Kohmura, K.; Oguni, N. Synlett 1991, 724. (e) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (f) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
4. For enantioselective ring-cleavage of epoxides, see: (a) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643. (b) Joshi, N. N.; Srebnik, M.; Brown, H. C. J. Am. Chem. Soc. 1988, 110, 6246. (c) Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213. (d) Hayashi, M.; Kohmura, K.; Oguni, N. Synlett 1991, 724. (e) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (f) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
5. For enantioselective ring-cleavage of epoxides, see: (a) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643. (b) Joshi, N. N.; Srebnik, M.; Brown, H. C. J. Am. Chem. Soc. 1988, 110, 6246. (c) Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213. (d) Hayashi, M.; Kohmura, K.; Oguni, N. Synlett 1991, 724. (e) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (f) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
6. For enantioselective ring-cleavage of epoxides, see: (a) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643. (b) Joshi, N. N.; Srebnik, M.; Brown, H. C. J. Am. Chem. Soc. 1988, 110, 6246. (c) Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213. (d) Hayashi, M.; Kohmura, K.; Oguni, N. Synlett 1991, 724. (e) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (f) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
7. For enantioselective ring-cleavage of epoxides, see: (a) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643. (b) Joshi, N. N.; Srebnik, M.; Brown, H. C. J. Am. Chem. Soc. 1988, 110, 6246. (c) Yamashita, H. Bull. Chem. Soc. Jpn. 1988, 61, 1213. (d) Hayashi, M.; Kohmura, K.; Oguni, N. Synlett 1991, 724. (e) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (f) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
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15. For recent mechanistic studies, see ref 3a and: (a) Denmark, S. E.; Willson, T. M. J. Am. Chem. Soc. 1989, 111, 3475. (b) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (c) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1991, 56, 6458. (d) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089. (e) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (f) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
16. For recent mechanistic studies, see ref 3a and: (a) Denmark, S. E.; Willson, T. M. J. Am. Chem. Soc. 1989, 111, 3475. (b) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (c) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1991, 56, 6458. (d) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089. (e) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (f) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
17. For recent mechanistic studies, see ref 3a and: (a) Denmark, S. E.; Willson, T. M. J. Am. Chem. Soc. 1989, 111, 3475. (b) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (c) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1991, 56, 6458. (d) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089. (e) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (f) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
18. For recent mechanistic studies, see ref 3a and: (a) Denmark, S. E.; Willson, T. M. J. Am. Chem. Soc. 1989, 111, 3475. (b) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (c) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1991, 56, 6458. (d) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089. (e) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (f) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
19. For recent mechanistic studies, see ref 3a and: (a) Denmark, S. E.; Willson, T. M. J. Am. Chem. Soc. 1989, 111, 3475. (b) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (c) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1991, 56, 6458. (d) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089. (e) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (f) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
20. (a) Review; Harada, T.; Oku, A. Synlett 1994, 95.
21. (b) Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346.
22. Kinugasa, M.; Harada, T.; Fujita, K.; Oku, A. Synlett 1996, 43.
23. 8 and N-tosylamino acids.
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35. The structures 8a and 8b are drawn to show the coordination of 1,3-dioxolanes to the bottom and upper faces of the complex, respectively. Conformation around the B-O(dioxolane) bond is beyond the scope of the present consideration.
36. 9e
37. Behforouz, M.; Zarrinmayeh, H.; Ogle, M. E.; Riehle, T. J.; Bell, F. W. J. Heterocycl. Chem. 1988, 25, 1627.
38. 2) δ 31.3.
39. 2, 10% ethyl acetate/hexane) gave 49.3 mg (86% yield) of 5b, whose ee was determined to be 91% after conversion to a (S)-MTPA ester derivative.
40. van der Gen, A.; Wiedhaup, K.; Swoboda, J. J.; Dunathan, H. C.; Johnson, W. S. J. Am. Chem. Soc. 1973, 95, 2656.