A Catalytic Deprotection of S,S-, S,O- and O,O-Acetals Using Bi(NO3)3·5 H2O under Air

Advanced Synthesis and Catalysis

Volumn 343, Issue 5, 2001, Pages 473-480

  Komatsu, Naoki ^a   Taniguchi, Azusa ^a   Wada, Shinobu ^b   Suzuki, Hitomi ^b  

^a KYOTO UNIVERSITY   (Japan)

^b KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

Acetals; Bismuth nitrate; Deprotection; Oxidation; Protecting groups; Reaction mechanisms

Indexed keywords

EID: 0141435778     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200107)343:5<473::aid-adsc473>3.3.co;2-f     Document Type: Article

References (52)

1. N. Komatsu, M. Uda, H. Suzuki, Synlett 1995, 984-986 and references cited therein.
2. (a) P. C. B. Page, M. B. van Niel, J. C. Prodger, Tetrahedron 1989, 45, 7643-7677;
3. (b) B.-T. Gröbel, D. Seebach, Synthesis 1977, 357-402;
4. (c) D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237;
5. (d) W. Howson, H. M. I. Osborn, J. Sweeney, J. Chem. Soc., Perkin Trans. 1 1995, 2439-2445.
6. (a) Radicicol: R. M. Garbaccio, S. J. Danishefsky, Org. Lett. 2000, 2, 3127-3129;
7. (b) Swinholide A: K. C. Nicolaou, A. P. Patron, K. Ajito, P. K. Richter, H. Khatuya, P. Bertinato, R. A. Miller, M. J. Tomaszewski, Chem. Eur. J. 1996, 2, 847-868;
8. (c) (-)-Stenine: Y. Morimoto, M. Iwahashi, K. Nishida, Y. Hayashi, H. Shirahama, Angew. Chem. Int. Ed. Engl. 1996, 35, 904-906;
9. (d) Zaragozic acid: K. C. Nicolaou, A. Nadin, J. E. Leresche, E. W. Yue, S. L. Greca, Angew. Chem. Int. Ed. Engl. 1994, 33, 2190-2191.
10. For recent examples, see: (a) M. Kimura, H. Kawai, Y. Sawaki, Electrochimica Acta 1997, 42, 497-500; (b) M. Kamata, Y. Murakami, Y. Tamagawa, M. Kato, E. Hasegawa, Tetrahedron 1994, 50, 12821-12828; (c) G. A. Epling, Q. Wang, Tetrahedron Lett. 1992, 33, 5909-5912.
11. For recent examples, see: (a) M. Kimura, H. Kawai, Y. Sawaki, Electrochimica Acta 1997, 42, 497-500; (b) M. Kamata, Y. Murakami, Y. Tamagawa, M. Kato, E. Hasegawa, Tetrahedron 1994, 50, 12821-12828; (c) G. A. Epling, Q. Wang, Tetrahedron Lett. 1992, 33, 5909-5912.
12. For recent examples, see: (a) M. Kimura, H. Kawai, Y. Sawaki, Electrochimica Acta 1997, 42, 497-500; (b) M. Kamata, Y. Murakami, Y. Tamagawa, M. Kato, E. Hasegawa, Tetrahedron 1994, 50, 12821-12828; (c) G. A. Epling, Q. Wang, Tetrahedron Lett. 1992, 33, 5909-5912.
13. For reviews, see: (a) T. W. Greene, P. G. Wuts, Protecting Groups in Organic Synthesis, 3rd Ed., John Wiley & Sons, Inc., New York, 1999, pp. 329-347; (b) S. Pawlenko, S. Lang-Fugmann, Methoden der Organischen Chemie (Houben-Weyl), 4th Edn., Georg Thieme Verlag, Stuttgart, 1992, pp. 481-482; (c) E. J. Corey, B. W. Erickson, J. Org. Chein. 1971, 36, 3553-3560.
14. For reviews, see: (a) T. W. Greene, P. G. Wuts, Protecting Groups in Organic Synthesis, 3rd Ed., John Wiley & Sons, Inc., New York, 1999, pp. 329-347; (b) S. Pawlenko, S. Lang-Fugmann, Methoden der Organischen Chemie (Houben-Weyl), 4th Edn., Georg Thieme Verlag, Stuttgart, 1992, pp. 481-482; (c) E. J. Corey, B. W. Erickson, J. Org. Chein. 1971, 36, 3553-3560.
15. For reviews, see: (a) T. W. Greene, P. G. Wuts, Protecting Groups in Organic Synthesis, 3rd Ed., John Wiley & Sons, Inc., New York, 1999, pp. 329-347; (b) S. Pawlenko, S. Lang-Fugmann, Methoden der Organischen Chemie (Houben-Weyl), 4th Edn., Georg Thieme Verlag, Stuttgart, 1992, pp. 481-482; (c) E. J. Corey, B. W. Erickson, J. Org. Chein. 1971, 36, 3553-3560.
16. To the best of our knowledge, two examples of catalytic deprotection have been reported previously: (a) T. Ravindranathan, S. P. Chavan, R. B. Tejwani, J. P. Varghese, J. Chem. Soc., Chem. Commun. 1991, 1750-1751; (b) G. A. Olah, S. C. Narang, G. F. Salem, B. G. B. Gupta, Synthesis 1979, 273-274.
17. To the best of our knowledge, two examples of catalytic deprotection have been reported previously: (a) T. Ravindranathan, S. P. Chavan, R. B. Tejwani, J. P. Varghese, J. Chem. Soc., Chem. Commun. 1991, 1750-1751; (b) G. A. Olah, S. C. Narang, G. F. Salem, B. G. B. Gupta, Synthesis 1979, 273-274.
18. N. Komatsu in Organobismuth Chemistry (Eds.: H. Suzuki, Y. Matano), Elsevier, Amsterdam, 2001, Chap. 5 and references cited therein.
19. N. Komatsu, A. Taniguchi, M. Uda, H. Suzuki, Chem. Commun. 1996, 1847-1848.
20. Bismuth salts are of low toxicity, see: H. Suzuki in Organobismuth Chemistry (Eds.: H. Suzuki, Y. Matano), Elsevier, Amsterdam, 2001, Chap. 1 and references cited therein.
21. [8] is corrected to an equimolar amount in this paper.
22. N. Komatsu, M. Uda, H. Suzuki, Chem. Lett. 1997, 1229-1230.
23. N. Komatsu, M. Uda, H. Suzuki, unpublished result.
24. (a) O. Kölln, H. Redlich, H. Frank, Synthesis 1995, 1383-1388;
25. (b) A.-M. Martre, G. Mousset, R. B. Rhlid, H. Veschambre, Tetrahedron Lett. 1990, 31, 2599-2602;
26. (c) J. A. Katzenellenbogen, S. B. Bowlus, J. Org. Chem. 1973, 38, 627-632;
27. (d) E. J. Corey, D. Seebach, Angew. Chem. Int. Ed. Engl. 1965, 4, 1077-1078.
28. A few examples of catalytic deprotection have been reported to date: (a) M. Kirihara, Y. Ochiai, N. Arai, S. Takizawa, T. Momose, H. Nemoto, Tetrahedron Lett. 1999, 40, 9055-9057; (b) T. Ravindranathan, S. P. Chavan, J. P. Varghese, S. W. Dantale, R. B. Tejwani, J. Chem. Soc., Chem. Commun. 1994, 1937-1938.
29. A few examples of catalytic deprotection have been reported to date: (a) M. Kirihara, Y. Ochiai, N. Arai, S. Takizawa, T. Momose, H. Nemoto, Tetrahedron Lett. 1999, 40, 9055-9057; (b) T. Ravindranathan, S. P. Chavan, J. P. Varghese, S. W. Dantale, R. B. Tejwani, J. Chem. Soc., Chem. Commun. 1994, 1937-1938.
30. K. J. Eash, M. S. Pulia, L. C. Wieland, R. S. Mohan, J. Org. Chem. 2000, 65, 8399-8401.
31. T. Cseri, S. Békássy, G. Kenessey, G. Liptay, F. Figueras, Themochimica Acta 1996, 288, 137-154.
32. (a) S. Samajdar, F. F. Becker, B. K. Banik, Tetrahedron Lett. 2000, 41, 8017-8020;
33. (b) S. Bekassy, T. Cseri, M. Horvath, J. Farkas, F. Figueras, New J. Chem. 1998, 22, 339-342;
34. (c) S. H. Mashraqui, M. A. Karnik, Synthesis 1998, 713-714;
35. (d) A. Cornélis, L. Delaude, A. Gerstmans, P. Laszlo, Tetrahedron Lett. 1988, 29, 5909-5912.
36. S. H. Mashraqui, C. D. Mudalier, M. A. Karnik, Synth. Commun. 1998, 28, 939-943.
37. S. A. Tymonko, B. A. Nattier, R. S. Mohan, Tetrahedron Lett. 1999, 40, 7657-7659.
38. (a) H. Firouzabadi, N. Iranpoor, M. A. Zolfigol, Bull. Chem. Soc. Jpn. 1998, 71, 2169-2173;
39. (b) G. Mehta, R. Uma, Tetrahedron Lett. 1996, 37, 1897-1898;
40. (c) C. York, G. K. S. Prakash, G. A. Olah, Tetrahedron 1996, 52, 9-14;
41. (d) M. T. M. El-Wassimy, K. A. Jorgensen, S.-O. Lawesson, J. Chem. Soc., Perkin Trans. 1 1983, 2201-2203.
42. (a) A. Boughriet, C. Brémard, M. Wartel, Nouv. J. Chim. 1987, 11, 245-251;
43. (b) A. Boughriet, M. Wartel, J.-C. Ficher, Can. J. Chem. 1986, 64, 5-10;
44. (c) C. C. Addison, Chem. Rev. 1980, 80, 21-39.
45. H. W. Lucien, J. Am. Chem. Soc. 1958, 80, 4458-4460.
46. E. Bosch, J. K. Kochi, J. Org. Chem. 1995, 60, 3172-3183 and references cited therein.
47. (a) D. L. H. Williams, Chem. Commun. 1996, 1085-1091;
48. (b) W. A. Pryor, D. F. Church, C. K. Govindan, G. Crank, J. Org. Chem. 1982, 47, 156-159;
49. (c) S. Oae, K. Shinhama, K. Fujimori, Y. H. Kim. Bull. Chem. Soc. Jpn. 1980, 53, 775-784;
50. (d) S. Oae, Y. H. Kim, D. Fukushima, K. Shinhama, J. Chem. Soc., Perkin Trans. 1 1978, 913-917;
51. (e) S. Oae, Y. H. Kim, D. Fukushima, T. Tanaka, Chem. Lett. 1977, 893-896.
52. B. Karimi, H. Seradj, Synlett 2000, 805-806.