Polymer-supported dicyanoketene acetal as a π-acid catalyst: Monothioacetalization and carbon-carbon bond formation of acetals

Chemical and Pharmaceutical Bulletin

Volumn 48, Issue 7, 2000, Pages 1010-1016

  Tanaka, Nobuyuki ^a   Miura, Tsuyoshi ^a   Masaki, Yukio ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Carbon carbon bond formation; Monothioacctalization; Polymeric dicyanoketene acetal; Recyclable catalyst; acid

Indexed keywords

ACETAL; COPOLYMER; ETHYLENE GLYCOL; POLYMER; STYRENE;

ARTICLE; CATALYST; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; POLYMERIZATION; REACTION ANALYSIS;

EID: 0033914330     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.48.1010     Document Type: Article

References (55)

1. a) Merrifield B., Science, 232, 341-347 (1986) and references cited therein;
2. b) Reviews: Akelah A., Sherrington D. C., Chem. Rev., 81, 557-587 (1981); Fréchet J. M. J., Tetrahedron, 37, 663-683 (1981); Shuttleworth S. J., Allin S. M., Sharma P. K., Synthesis, 1997, 1217 1239.
3. b) Reviews: Akelah A., Sherrington D. C., Chem. Rev., 81, 557-587 (1981); Fréchet J. M. J., Tetrahedron, 37, 663-683 (1981); Shuttleworth S. J., Allin S. M., Sharma P. K., Synthesis, 1997, 1217 1239.
4. b) Reviews: Akelah A., Sherrington D. C., Chem. Rev., 81, 557-587 (1981); Fréchet J. M. J., Tetrahedron, 37, 663-683 (1981); Shuttleworth S. J., Allin S. M., Sharma P. K., Synthesis, 1997, 1217 1239.
5. a) Onaka M., Sugita K., Izumi Y., Chem. Lett., 1986, 1327-1328;
6. b) Clark J. H., Martin K., Teasdale A. J., Barlow S. J., J. Chem. Soc., Chem. Commun., 1995, 2037-2040; Villemin D., Martin B., J. Chem. Res. (S), 1994, 146-147;
7. b) Clark J. H., Martin K., Teasdale A. J., Barlow S. J., J. Chem. Soc., Chem. Commun., 1995, 2037-2040; Villemin D., Martin B., J. Chem. Res. (S), 1994, 146-147;
8. c) Iranpoor N., Tarrian T., Movahedi Z., Synthesis, 1996, 1473-1476;
9. d) Kobayashi S., Nagayama S., J. Org. Chem., 61, 2256-2257 (1996); Tamami B., Iranpoor N., Zarchi M. A. K., Polymer, 34, 2011-2013 (1993).
10. d) Kobayashi S., Nagayama S., J. Org. Chem., 61, 2256-2257 (1996); Tamami B., Iranpoor N., Zarchi M. A. K., Polymer, 34, 2011-2013 (1993).
11. a) Kobayashi S., Nagayama S., Synlett, 1997, 653-654; Nagahara S., Maruoka K., Yamamoto H., Chem. Lett., 1992, 1193-1196;
12. a) Kobayashi S., Nagayama S., Synlett, 1997, 653-654; Nagahara S., Maruoka K., Yamamoto H., Chem. Lett., 1992, 1193-1196;
13. b) Otera J., Niibo Y., Tatsumi N., Nozaki H., J. Org. Chem., 53, 275-278 (1988).
14. a) Kumar P., Dinesh C. U., Reddy R. S., Pandey B., Synthesis, 1993, 1069-1070; Takeuchi H., Kitajima K., Yamamoto Y., Mizuno K., J. Chem. Soc., Perkin Trans. 2, 1993, 199-203;
15. a) Kumar P., Dinesh C. U., Reddy R. S., Pandey B., Synthesis, 1993, 1069-1070; Takeuchi H., Kitajima K., Yamamoto Y., Mizuno K., J. Chem. Soc., Perkin Trans. 2, 1993, 199-203;
16. b) Hoyer S., Laszlo P., Synthesis, 1986, 655-657;
17. c) Johnston R. D., Marston C. R., Krieger P. E., Goe G. L., Synthesis, 1988, 393-394;
18. d) Olah G. A., Husain A., Singh B. P., Synthesis, 1983, 892-895;
19. e) Svec F., Bares M., Zajic J., Kálal J., Chem. Ind., 1977, 159.
20. Mukaiyama T., Iwakiri H., Chem. Lett., 1985, 1363-1366.
21. a) Masaki Y., Miura T., Ochiai M., Synlett, 1993, 847-849;
22. b) Masaki Y., Miura T., Ochiai M., Chem. Lett., 1993, 17-20;
23. c) Miura T., Masaki Y., J. Chem. Soc., Perkin Trans. 1, 1994, 1659-1660;
24. d) Miura T., Masaki Y., J. Chem. Soc., Perkin Trans. 1, 1995, 2155-2158.
25. a) Miura T., Masaki Y., Chem. Pharm. Bull., 43, 523-525 (1995); Masaki Y., Miura T., Ochiai M., Bull. Chem. Soc., Jpn., 69, 195-205 (1996);
26. a) Miura T., Masaki Y., Chem. Pharm. Bull., 43, 523-525 (1995); Masaki Y., Miura T., Ochiai M., Bull. Chem. Soc., Jpn., 69, 195-205 (1996);
27. b) Miura T., Masaki Y., Synth. Commun., 25, 1981-1987 (1995);
28. c) Miura T., Masaki Y., Tetrahedron Lett., 35, 7961-7964 (1994); Tetrahedron, 51, 10477-10486 (1995).
29. c) Miura T., Masaki Y., Tetrahedron Lett., 35, 7961-7964 (1994); Tetrahedron, 51, 10477-10486 (1995).
30. a) Masaki Y., Tanaka N., Miura T., Tetrahedron Lett., 39, 5799-5802 (1998);
31. b) Tanaka N., Masaki Y., Synlett, 1999, 1277-1279.
32. c) Tanaka N., Masaki Y., Synlett. 1999, 1960-1962.
33. Middleton W. J., Engelhardt V. A., J. Am. Chem. Soc., 80, 2788-2795 (1958).
34. Minutolo F., Pini D., Salvadori P., Tetrahedron Lett., 37, 3375-3378 (1996).
35. De B. B., Lohray B. B., Sivaram S., Dhai P. K., Tetrahedron Asymmetry, 6, 2105-2108 (1995).
36. The most convenient method for preparation of saturated monothioacetals is the transacetalization of acetals. a) Nakatsubo F., Cocuzza A. J., Keeley D. E., Kishi Y., J. Am. Chem. Soc., 99, 4835-4836 (1977); Kieczykowski G. R., Schlessinger R. H., J. Am. Chem. Soc., 100, 1938-1940 (1978); Naruto M., Ohno K., Naruse N., Chem. Lett., 1978, 1419-1422;
37. The most convenient method for preparation of saturated monothioacetals is the transacetalization of acetals. a) Nakatsubo F., Cocuzza A. J., Keeley D. E., Kishi Y., J. Am. Chem. Soc., 99, 4835-4836 (1977); Kieczykowski G. R., Schlessinger R. H., J. Am. Chem. Soc., 100, 1938-1940 (1978); Naruto M., Ohno K., Naruse N., Chem. Lett., 1978, 1419-1422;
38. The most convenient method for preparation of saturated monothioacetals is the transacetalization of acetals. a) Nakatsubo F., Cocuzza A. J., Keeley D. E., Kishi Y., J. Am. Chem. Soc., 99, 4835-4836 (1977); Kieczykowski G. R., Schlessinger R. H., J. Am. Chem. Soc., 100, 1938-1940 (1978); Naruto M., Ohno K., Naruse N., Chem. Lett., 1978, 1419-1422;
39. b) Kim S., Park J. H., Lee S., Tetrahedron Lett., 30, 6697-6700 (1989);
40. c) Morton H. E., Guindon Y., J. Org. Chem., 50, 5379-5382 (1985); Guindon Y., Bernstein M. A., Anderson P. C., Tetrahedron Lett., 28, 2225-2228 (1987);
41. c) Morton H. E., Guindon Y., J. Org. Chem., 50, 5379-5382 (1985); Guindon Y., Bernstein M. A., Anderson P. C., Tetrahedron Lett., 28, 2225-2228 (1987);
42. d) Sato T., Kobayashi T., Gojo T., Yoshida E., Otera J., Nozaki H., Chem. Lett., 1987, 1661-1664; Sato T., Otera J., Nozaki H., Tetrahedron, 45, 1209-1218 (1989);
43. d) Sato T., Kobayashi T., Gojo T., Yoshida E., Otera J., Nozaki H., Chem. Lett., 1987, 1661-1664; Sato T., Otera J., Nozaki H., Tetrahedron, 45, 1209-1218 (1989);
44. e) Masaki Y., Serizawa Y., Kaji K., Chem. Lett., 1985, 1933-1936.
45. In recent years, a variety of efficient catalysts or promoters have been developed to induce carbon-carbon bond forming reactions of aldehydes, ketones, and acetals with silylated nucleophiles. a) McCluskey A., Mayer D. M., Young D. J., Tetrahedron Lett., 38, 5217-5218 (1997);
46. b) Ooi T., Tayama E., Takahashi M., Maruoka K., Tetrahedron Lett., 38, 7403-7406 (1997);
47. c) Ishii A., Kotera O., Saeki T., Mikami K., Synlett, 1997, 1145-1146;
48. d) Soga T., Takenoshita H., Yamada M., Han J. S., Mukaiyama T., Bull. Chem. Soc. Jpn., 64, 1108-1117 (1991);
49. e) Soga T., Takenoshita H., Yamada M., Mukaiyama T., Bull. Chem. Soc. Jpn., 63, 3122-3131 (1990);
50. f) Sato T., Otera J., Nozaki H., J. Am. Chem. Soc., 112, 901-902 (1990) and references cited therein.
51. Nelson B. A., Hodges E. J., Simon J. I., J. Org. Chem., 1956, 798-799.
52. Williams N., Ber. Dtsch. Chem. Ges., 60, 2509-2514 (1927).
53. Torii S., Inokuchi T., Takagishi S., Horike H., Kuroda H., Uneyama K., Bull. Chem. Soc. Jpn., 60, 2173-2188 (1987).
54. Inagaki M., Hatanaka A., Mimura M., Hiratake J., Nishioka T., Oda J., Bull. Chem. Soc. Jpn., 65, 111-120 (1992).
55. Higuchi K., Onaka M., Izumi Y., Bull. Chem. Soc. Jpn., 66, 2016-2032 (1993).