Highly Selective Ring-Cleavage of Acetals Catalyzed by Phenylboron Complexes Derived from Sulfonamides of α-Amino Acids

Synlett

Volumn 1996, Issue 1, 1996, Pages 43-45

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

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002861435     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5332     Document Type: Article

References (39)

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3. (c) Bartlett, P.A.; Johnson, W. S.; Elliott, J. D. J. Am. Chem. Soc. 1983, 105, 2088.
4. For a recent review, see: (d) Alexakis, A.; Mangency, P. Tetrahedron Asymmetry 1990, 1, 477. (e) Seebach, D.; Imwinkelreid, R.; Weber, T. In Modem Synthetic Methods; Scheffold, R., Ed.; Springer Verlag: Berlin, 1986; Vol. 4; p 125.
5. For a recent review, see: (d) Alexakis, A.; Mangency, P. Tetrahedron Asymmetry 1990, 1, 477. (e) Seebach, D.; Imwinkelreid, R.; Weber, T. In Modem Synthetic Methods; Scheffold, R., Ed.; Springer Verlag: Berlin, 1986; Vol. 4; p 125.
6. For leading references, see also: (f) Ishihara, K.; Hanaki, N.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10695. (g) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089.
7. For leading references, see also: (f) Ishihara, K.; Hanaki, N.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10695. (g) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089.
8. For recent mechanistic studies, see reference 1g 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) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (e) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
9. For recent mechanistic studies, see reference 1g 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) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (e) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
10. For recent mechanistic studies, see reference 1g 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) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (e) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
11. For recent mechanistic studies, see reference 1g 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) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (e) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
12. For recent mechanistic studies, see reference 1g 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) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (e) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
13. (a) Harada, T.; Hayashiya, T.; Wada, I, Iwa-ake, N.; Oku, A. J. Am. Chem. Soc. 1987, 109, 527.
14. For a review, see: (b) Harada, T.; Oku, A. Synlett 1994, 95.
15. A reductive cleavage of chiral cyclic acetals catalyzed by an aluminum catalyst has been reported: Ishihara, K.; Hanaki, N, Yamamoto, H. Synlett 1993, 127 and reference 1f.
16. For Lewis acid-catalyzed cleavage acyclic acetals, see; (a) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 71. (b) Sakurai, H.; Sasaki, K.; Hosomi, A. Tetrahedron Lett. 1981, 22, 745. (c) Mukaiyama, T.; Nagaoka, H.; Murakami, M.; Ohshima, M. Chem. Lett. 1985, 977.
17. For Lewis acid-catalyzed cleavage acyclic acetals, see; (a) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 71. (b) Sakurai, H.; Sasaki, K.; Hosomi, A. Tetrahedron Lett. 1981, 22, 745. (c) Mukaiyama, T.; Nagaoka, H.; Murakami, M.; Ohshima, M. Chem. Lett. 1985, 977.
18. For Lewis acid-catalyzed cleavage acyclic acetals, see; (a) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 71. (b) Sakurai, H.; Sasaki, K.; Hosomi, A. Tetrahedron Lett. 1981, 22, 745. (c) Mukaiyama, T.; Nagaoka, H.; Murakami, M.; Ohshima, M. Chem. Lett. 1985, 977.
19. (a) Choi, V. M.; Elliott, J. D.; Johnson, W. S. Tetrahedron Lett. 1984, 25, 591.
20. (b) Silverman, I. R.; Edington, C.; Elliott, J. D.; Johnson, W. S. J. Org. Chem. 1987, 52, 180.
21. (a) Takasu, M.; Yamamoto, H. Synlett 1990, 194.
22. (b) Sartor, D.; Saffrich, J.; Helmchen, G. Synlett 1990, 197.
23. (a) Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276.
24. (b) Parmee, E. R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365.
25. (c) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729.
26. (d) Kiyooka, S.; Kaneko, Y.; Kume, K. Tetrahedron Lett. 1992, 33, 4927.
27. (e) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
28. For mechanistic studies on the silyl group migration, see: (a) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323. (b) Denmark, S. E.; Chen, C.-T. Tetrahedron Lett. 1994, 35, 4327. (c) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
29. For mechanistic studies on the silyl group migration, see: (a) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323. (b) Denmark, S. E.; Chen, C.-T. Tetrahedron Lett. 1994, 35, 4327. (c) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
30. For mechanistic studies on the silyl group migration, see: (a) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323. (b) Denmark, S. E.; Chen, C.-T. Tetrahedron Lett. 1994, 35, 4327. (c) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
31. 2) δ 48.3.
32. In the reaction using 5a as a catalyst, the formation of 7a as well as that of 6 was detected at the early stage of the reaction by a GC analysis. No 7a was detected after 20 h of the reaction time.
33. 9
34. Reaction was nonstereoselective (anti:syn 63:37) when allyltrimethylsilane was used in place of 4e under similar conditions.
35. 2, 10% ethyl acetate/hexane) gave 101 mg (81 % yield) of the ring-cleavage product 7a (anti:syn 98:2).
36. Johnson, W. S.; Kelson, A. B.; Elliott, J. D. Tetrahedron Lett. 1988, 29, 3757.
37. 1H NMR (300M Hz) analysis of the (S)-MTPA ester derivative.
38. The reaction of rac-3a and 4a using 5d as a catalyst gave 7a (anti:syn = 95:5) in 80% yield.
39. Enantiomeric excess was established by capillary GC analysis using a chiral CP-Cyclodextrin-B-236-M-19 (25 m) column.