Ruthenium-catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines

Tetrahedron

Volumn 59, Issue 40, 2003, Pages 7997-8002

  Cho, Chan Sik ^a   Kim, Bok Tae ^a   Choi, Heung Jin ^a   Kim, Tae Jeong ^a   Shim, Sang Chul ^a  

^a Kyungpook National University   (South Korea)

Author keywords

2 aminobenzyl alcohol; Cyclization; Oxidative coupling; Quinolines; Ruthenium catalyst; Secondary alcohols

Indexed keywords

2 AMINOBENZAMIDE; ALCOHOL; QUINOLINE DERIVATIVE; RUTHENIUM;

ALCOHOL OXIDATION; ALDOL REACTION; ARTICLE; CATALYSIS; CYCLIZATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0141517572     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.027     Document Type: Article

References (59)

1. Arcadi A., Chiarini M., Giuseppe S.D., Marinelli F. Synlett. 2003;203. and references cited therein.
2. Jones G. Katritzky A.R., Rees C.W. Comprehensive Heterocyclic Chemistry. Vol. 2:1984;395 Pergamon, New York.
3. (a) Amii H., Kishikawa Y., Uneyama K. Org. Lett. 3:2001;1109. and references cited therein. (b) Cho C.S., Oh B.H., Kim J.S., Kim T.-J., Shim S.C. Chem. Commun. 2000;1885. and references cited therein.
4. (a) Amii H., Kishikawa Y., Uneyama K. Org. Lett. 3:2001;1109. and references cited therein. (b) Cho C.S., Oh B.H., Kim J.S., Kim T.-J., Shim S.C. Chem. Commun. 2000;1885. and references cited therein.
5. For the synthesis of indoles: Cho C.S., Lim H.K., Shim S.C., Kim T.J., Choi H.-J. Chem. Commun. 1998;995 Cho C.S., Kim J.H., Shim S.C. Tetrahedron Lett. 41:2000;1811 Cho C.S., Kim J.H., Kim T.-J., Shim S.C. Tetrahedron. 57:2001;3321 Cho C.S., Kim J.H., Choi H.-J., Kim T.-J., Shim S.C. Tetrahedron Lett. 44:2003;2975.
6. For the synthesis of indoles: Cho C.S., Lim H.K., Shim S.C., Kim T.J., Choi H.-J. Chem. Commun. 1998;995 Cho C.S., Kim J.H., Shim S.C. Tetrahedron Lett. 41:2000;1811 Cho C.S., Kim J.H., Kim T.-J., Shim S.C. Tetrahedron. 57:2001;3321 Cho C.S., Kim J.H., Choi H.-J., Kim T.-J., Shim S.C. Tetrahedron Lett. 44:2003;2975.
7. For the synthesis of indoles: Cho C.S., Lim H.K., Shim S.C., Kim T.J., Choi H.-J. Chem. Commun. 1998;995 Cho C.S., Kim J.H., Shim S.C. Tetrahedron Lett. 41:2000;1811 Cho C.S., Kim J.H., Kim T.-J., Shim S.C. Tetrahedron. 57:2001;3321 Cho C.S., Kim J.H., Choi H.-J., Kim T.-J., Shim S.C. Tetrahedron Lett. 44:2003;2975.
8. For the synthesis of indoles: Cho C.S., Lim H.K., Shim S.C., Kim T.J., Choi H.-J. Chem. Commun. 1998;995 Cho C.S., Kim J.H., Shim S.C. Tetrahedron Lett. 41:2000;1811 Cho C.S., Kim J.H., Kim T.-J., Shim S.C. Tetrahedron. 57:2001;3321 Cho C.S., Kim J.H., Choi H.-J., Kim T.-J., Shim S.C. Tetrahedron Lett. 44:2003;2975.
9. Cho C.S., Oh B.H., Shim S.C. Tetrahedron Lett. 40:1999;1499 Cho C.S., Oh B.H., Shim S.C. J. Heterocycl. Chem. 36:1999;1175 Cho C.S., Kim J.S., Oh B.H., Kim T.-J., Shim S.C. Tetrahedron. 56:2000;7747 Cho C.S., Kim T.K., Kim B.T., Kim T.-J., Shim S.C. J. Organomet. Chem. 650:2002;65 Cho C.S., Kim T.K., Choi H.-J., Kim T.-J., Shim S.C. Bull. Korean Chem. Soc. 23:2002;541.
10. Cho C.S., Oh B.H., Shim S.C. Tetrahedron Lett. 40:1999;1499 Cho C.S., Oh B.H., Shim S.C. J. Heterocycl. Chem. 36:1999;1175 Cho C.S., Kim J.S., Oh B.H., Kim T.-J., Shim S.C. Tetrahedron. 56:2000;7747 Cho C.S., Kim T.K., Kim B.T., Kim T.-J., Shim S.C. J. Organomet. Chem. 650:2002;65 Cho C.S., Kim T.K., Choi H.-J., Kim T.-J., Shim S.C. Bull. Korean Chem. Soc. 23:2002;541.
11. Cho C.S., Oh B.H., Shim S.C. Tetrahedron Lett. 40:1999;1499 Cho C.S., Oh B.H., Shim S.C. J. Heterocycl. Chem. 36:1999;1175 Cho C.S., Kim J.S., Oh B.H., Kim T.-J., Shim S.C. Tetrahedron. 56:2000;7747 Cho C.S., Kim T.K., Kim B.T., Kim T.-J., Shim S.C. J. Organomet. Chem. 650:2002;65 Cho C.S., Kim T.K., Choi H.-J., Kim T.-J., Shim S.C. Bull. Korean Chem. Soc. 23:2002;541.
12. Cho C.S., Oh B.H., Shim S.C. Tetrahedron Lett. 40:1999;1499 Cho C.S., Oh B.H., Shim S.C. J. Heterocycl. Chem. 36:1999;1175 Cho C.S., Kim J.S., Oh B.H., Kim T.-J., Shim S.C. Tetrahedron. 56:2000;7747 Cho C.S., Kim T.K., Kim B.T., Kim T.-J., Shim S.C. J. Organomet. Chem. 650:2002;65 Cho C.S., Kim T.K., Choi H.-J., Kim T.-J., Shim S.C. Bull. Korean Chem. Soc. 23:2002;541.
13. Cho C.S., Oh B.H., Shim S.C. Tetrahedron Lett. 40:1999;1499 Cho C.S., Oh B.H., Shim S.C. J. Heterocycl. Chem. 36:1999;1175 Cho C.S., Kim J.S., Oh B.H., Kim T.-J., Shim S.C. Tetrahedron. 56:2000;7747 Cho C.S., Kim T.K., Kim B.T., Kim T.-J., Shim S.C. J. Organomet. Chem. 650:2002;65 Cho C.S., Kim T.K., Choi H.-J., Kim T.-J., Shim S.C. Bull. Korean Chem. Soc. 23:2002;541.
14. For transition metal-catalyzed amine exchange reaction, see: Yoshimura N., Moritani I., Shimamura T., Murahashi S.-I. J. Am. Chem. Soc. 95:1973;3038 Murahashi S.-I., Hirano T., Yano T. J. Am. Chem. Soc. 100:1978;348 Shvo Y., Laine R.M. J. Chem. Soc., Chem. Commun. 1980;753 Khai B.-T., Concilio C., Porzi G. J. Organomet. Chem. 208:1981;249 Khai B.-T., Concilio C., Porzi G. J. Org. Chem. 46:1981;1759 Arcelli A., Khai B.-T., Porzi G. J. Organomet. Chem. 231:1982;C31 Murahashi S.-I., Kondo K., Hakata T. Tetrahedron Lett. 23:1982;229 Laine R.M., Thomas D.W., Cary L.W. J. Am. Chem. Soc. 104:1982;1763 Jung C.W., Fellmann J.D., Garrou P.E. Organometallics. 2:1983;1042 Murahashi S.-I. Angew. Chem. Int. Ed. 34:1995;2443.
15. For transition metal-catalyzed amine exchange reaction, see: Yoshimura N., Moritani I., Shimamura T., Murahashi S.-I. J. Am. Chem. Soc. 95:1973;3038 Murahashi S.-I., Hirano T., Yano T. J. Am. Chem. Soc. 100:1978;348 Shvo Y., Laine R.M. J. Chem. Soc., Chem. Commun. 1980;753 Khai B.-T., Concilio C., Porzi G. J. Organomet. Chem. 208:1981;249 Khai B.-T., Concilio C., Porzi G. J. Org. Chem. 46:1981;1759 Arcelli A., Khai B.-T., Porzi G. J. Organomet. Chem. 231:1982;C31 Murahashi S.-I., Kondo K., Hakata T. Tetrahedron Lett. 23:1982;229 Laine R.M., Thomas D.W., Cary L.W. J. Am. Chem. Soc. 104:1982;1763 Jung C.W., Fellmann J.D., Garrou P.E. Organometallics. 2:1983;1042 Murahashi S.-I. Angew. Chem. Int. Ed. 34:1995;2443.
16. For transition metal-catalyzed amine exchange reaction, see: Yoshimura N., Moritani I., Shimamura T., Murahashi S.-I. J. Am. Chem. Soc. 95:1973;3038 Murahashi S.-I., Hirano T., Yano T. J. Am. Chem. Soc. 100:1978;348 Shvo Y., Laine R.M. J. Chem. Soc., Chem. Commun. 1980;753 Khai B.-T., Concilio C., Porzi G. J. Organomet. Chem. 208:1981;249 Khai B.-T., Concilio C., Porzi G. J. Org. Chem. 46:1981;1759 Arcelli A., Khai B.-T., Porzi G. J. Organomet. Chem. 231:1982;C31 Murahashi S.-I., Kondo K., Hakata T. Tetrahedron Lett. 23:1982;229 Laine R.M., Thomas D.W., Cary L.W. J. Am. Chem. Soc. 104:1982;1763 Jung C.W., Fellmann J.D., Garrou P.E. Organometallics. 2:1983;1042 Murahashi S.-I. Angew. Chem. Int. Ed. 34:1995;2443.
17. For transition metal-catalyzed amine exchange reaction, see: Yoshimura N., Moritani I., Shimamura T., Murahashi S.-I. J. Am. Chem. Soc. 95:1973;3038 Murahashi S.-I., Hirano T., Yano T. J. Am. Chem. Soc. 100:1978;348 Shvo Y., Laine R.M. J. Chem. Soc., Chem. Commun. 1980;753 Khai B.-T., Concilio C., Porzi G. J. Organomet. Chem. 208:1981;249 Khai B.-T., Concilio C., Porzi G. J. Org. Chem. 46:1981;1759 Arcelli A., Khai B.-T., Porzi G. J. Organomet. Chem. 231:1982;C31 Murahashi S.-I., Kondo K., Hakata T. Tetrahedron Lett. 23:1982;229 Laine R.M., Thomas D.W., Cary L.W. J. Am. Chem. Soc. 104:1982;1763 Jung C.W., Fellmann J.D., Garrou P.E. Organometallics. 2:1983;1042 Murahashi S.-I. Angew. Chem. Int. Ed. 34:1995;2443.
18. For transition metal-catalyzed amine exchange reaction, see: Yoshimura N., Moritani I., Shimamura T., Murahashi S.-I. J. Am. Chem. Soc. 95:1973;3038 Murahashi S.-I., Hirano T., Yano T. J. Am. Chem. Soc. 100:1978;348 Shvo Y., Laine R.M. J. Chem. Soc., Chem. Commun. 1980;753 Khai B.-T., Concilio C., Porzi G. J. Organomet. Chem. 208:1981;249 Khai B.-T., Concilio C., Porzi G. J. Org. Chem. 46:1981;1759 Arcelli A., Khai B.-T., Porzi G. J. Organomet. Chem. 231:1982;C31 Murahashi S.-I., Kondo K., Hakata T. Tetrahedron Lett. 23:1982;229 Laine R.M., Thomas D.W., Cary L.W. J. Am. Chem. Soc. 104:1982;1763 Jung C.W., Fellmann J.D., Garrou P.E. Organometallics. 2:1983;1042 Murahashi S.-I. Angew. Chem. Int. Ed. 34:1995;2443.
19. For transition metal-catalyzed amine exchange reaction, see: Yoshimura N., Moritani I., Shimamura T., Murahashi S.-I. J. Am. Chem. Soc. 95:1973;3038 Murahashi S.-I., Hirano T., Yano T. J. Am. Chem. Soc. 100:1978;348 Shvo Y., Laine R.M. J. Chem. Soc., Chem. Commun. 1980;753 Khai B.-T., Concilio C., Porzi G. J. Organomet. Chem. 208:1981;249 Khai B.-T., Concilio C., Porzi G. J. Org. Chem. 46:1981;1759 Arcelli A., Khai B.-T., Porzi G. J. Organomet. Chem. 231:1982;C31 Murahashi S.-I., Kondo K., Hakata T. Tetrahedron Lett. 23:1982;229 Laine R.M., Thomas D.W., Cary L.W. J. Am. Chem. Soc. 104:1982;1763 Jung C.W., Fellmann J.D., Garrou P.E. Organometallics. 2:1983;1042 Murahashi S.-I. Angew. Chem. Int. Ed. 34:1995;2443.
20. For transition metal-catalyzed amine exchange reaction, see: Yoshimura N., Moritani I., Shimamura T., Murahashi S.-I. J. Am. Chem. Soc. 95:1973;3038 Murahashi S.-I., Hirano T., Yano T. J. Am. Chem. Soc. 100:1978;348 Shvo Y., Laine R.M. J. Chem. Soc., Chem. Commun. 1980;753 Khai B.-T., Concilio C., Porzi G. J. Organomet. Chem. 208:1981;249 Khai B.-T., Concilio C., Porzi G. J. Org. Chem. 46:1981;1759 Arcelli A., Khai B.-T., Porzi G. J. Organomet. Chem. 231:1982;C31 Murahashi S.-I., Kondo K., Hakata T. Tetrahedron Lett. 23:1982;229 Laine R.M., Thomas D.W., Cary L.W. J. Am. Chem. Soc. 104:1982;1763 Jung C.W., Fellmann J.D., Garrou P.E. Organometallics. 2:1983;1042 Murahashi S.-I. Angew. Chem. Int. Ed. 34:1995;2443.
21. For transition metal-catalyzed amine exchange reaction, see: Yoshimura N., Moritani I., Shimamura T., Murahashi S.-I. J. Am. Chem. Soc. 95:1973;3038 Murahashi S.-I., Hirano T., Yano T. J. Am. Chem. Soc. 100:1978;348 Shvo Y., Laine R.M. J. Chem. Soc., Chem. Commun. 1980;753 Khai B.-T., Concilio C., Porzi G. J. Organomet. Chem. 208:1981;249 Khai B.-T., Concilio C., Porzi G. J. Org. Chem. 46:1981;1759 Arcelli A., Khai B.-T., Porzi G. J. Organomet. Chem. 231:1982;C31 Murahashi S.-I., Kondo K., Hakata T. Tetrahedron Lett. 23:1982;229 Laine R.M., Thomas D.W., Cary L.W. J. Am. Chem. Soc. 104:1982;1763 Jung C.W., Fellmann J.D., Garrou P.E. Organometallics. 2:1983;1042 Murahashi S.-I. Angew. Chem. Int. Ed. 34:1995;2443.
22. For transition metal-catalyzed amine exchange reaction, see: Yoshimura N., Moritani I., Shimamura T., Murahashi S.-I. J. Am. Chem. Soc. 95:1973;3038 Murahashi S.-I., Hirano T., Yano T. J. Am. Chem. Soc. 100:1978;348 Shvo Y., Laine R.M. J. Chem. Soc., Chem. Commun. 1980;753 Khai B.-T., Concilio C., Porzi G. J. Organomet. Chem. 208:1981;249 Khai B.-T., Concilio C., Porzi G. J. Org. Chem. 46:1981;1759 Arcelli A., Khai B.-T., Porzi G. J. Organomet. Chem. 231:1982;C31 Murahashi S.-I., Kondo K., Hakata T. Tetrahedron Lett. 23:1982;229 Laine R.M., Thomas D.W., Cary L.W. J. Am. Chem. Soc. 104:1982;1763 Jung C.W., Fellmann J.D., Garrou P.E. Organometallics. 2:1983;1042 Murahashi S.-I. Angew. Chem. Int. Ed. 34:1995;2443.
23. For transition metal-catalyzed amine exchange reaction, see: Yoshimura N., Moritani I., Shimamura T., Murahashi S.-I. J. Am. Chem. Soc. 95:1973;3038 Murahashi S.-I., Hirano T., Yano T. J. Am. Chem. Soc. 100:1978;348 Shvo Y., Laine R.M. J. Chem. Soc., Chem. Commun. 1980;753 Khai B.-T., Concilio C., Porzi G. J. Organomet. Chem. 208:1981;249 Khai B.-T., Concilio C., Porzi G. J. Org. Chem. 46:1981;1759 Arcelli A., Khai B.-T., Porzi G. J. Organomet. Chem. 231:1982;C31 Murahashi S.-I., Kondo K., Hakata T. Tetrahedron Lett. 23:1982;229 Laine R.M., Thomas D.W., Cary L.W. J. Am. Chem. Soc. 104:1982;1763 Jung C.W., Fellmann J.D., Garrou P.E. Organometallics. 2:1983;1042 Murahashi S.-I. Angew. Chem. Int. Ed. 34:1995;2443.
24. Cho C.S., Kim B.T., Kim T.-J., Shim S.C. Chem. Commun. 2001;2576.
25. Friedlaender P. Chem. Ber. 15:1882;2572. For a review, see: Cheng C.-C., Yan S.-J. Org. React. 28:1982;37. For a regioselective Friedlaender quinoline synthesis, see: Hsiao Y., Rivera N.R., Yasuda N., Hughes D.L., Reider P.J. Org. Lett. 3:2001;1101.
26. Friedlaender P. Chem. Ber. 15:1882;2572. For a review, see: Cheng C.-C., Yan S.-J. Org. React. 28:1982;37. For a regioselective Friedlaender quinoline synthesis, see: Hsiao Y., Rivera N.R., Yasuda N., Hughes D.L., Reider P.J. Org. Lett. 3:2001;1101.
27. Friedlaender P. Chem. Ber. 15:1882;2572. For a review, see: Cheng C.-C., Yan S.-J. Org. React. 28:1982;37. For a regioselective Friedlaender quinoline synthesis, see: Hsiao Y., Rivera N.R., Yasuda N., Hughes D.L., Reider P.J. Org. Lett. 3:2001;1101.
28. Cho C.S., Kim B.T., Kim T.-J., Shim S.C. Tetrahedron Lett. 43:2002;7987.
29. Cho C.S., Kim B.T., Kim T.-J., Shim S.C. J. Org. Chem. 66:2001;9020.
30. For recent reviews on transition metal-catalyzed transfer hydrogenation, see: Zassinovich G., Mestroni G., Gladiali S. Chem. Rev. 92:1992;1051 Bäckvall J.-E., Chowdhury R.L., Karlsson U., Wang G. Williams A.F., Floriani C., Merbach A.E. Perspectives in Coordination Chemistry. 1992;463-486 VCH, New York, Noyori R., Hashiguchi S. Acc. Chem. Res. 30:1997;97 Naota T., Takaya H., Murahashi S.-I. Chem. Rev. 98:1998;2599 Palmer M., Wills M. Tetrahedron: Asymmetry. 10:1999;2045.
31. For recent reviews on transition metal-catalyzed transfer hydrogenation, see: Zassinovich G., Mestroni G., Gladiali S. Chem. Rev. 92:1992;1051 Bäckvall J.-E., Chowdhury R.L., Karlsson U., Wang G. Williams A.F., Floriani C., Merbach A.E. Perspectives in Coordination Chemistry. 1992;463-486 VCH, New York, Noyori R., Hashiguchi S. Acc. Chem. Res. 30:1997;97 Naota T., Takaya H., Murahashi S.-I. Chem. Rev. 98:1998;2599 Palmer M., Wills M. Tetrahedron: Asymmetry. 10:1999;2045.
32. For recent reviews on transition metal-catalyzed transfer hydrogenation, see: Zassinovich G., Mestroni G., Gladiali S. Chem. Rev. 92:1992;1051 Bäckvall J.-E., Chowdhury R.L., Karlsson U., Wang G. Williams A.F., Floriani C., Merbach A.E. Perspectives in Coordination Chemistry. 1992;463-486 VCH, New York, Noyori R., Hashiguchi S. Acc. Chem. Res. 30:1997;97 Naota T., Takaya H., Murahashi S.-I. Chem. Rev. 98:1998;2599 Palmer M., Wills M. Tetrahedron: Asymmetry. 10:1999;2045.
33. For recent reviews on transition metal-catalyzed transfer hydrogenation, see: Zassinovich G., Mestroni G., Gladiali S. Chem. Rev. 92:1992;1051 Bäckvall J.-E., Chowdhury R.L., Karlsson U., Wang G. Williams A.F., Floriani C., Merbach A.E. Perspectives in Coordination Chemistry. 1992;463-486 VCH, New York, Noyori R., Hashiguchi S. Acc. Chem. Res. 30:1997;97 Naota T., Takaya H., Murahashi S.-I. Chem. Rev. 98:1998;2599 Palmer M., Wills M. Tetrahedron: Asymmetry. 10:1999;2045.
34. For recent reviews on transition metal-catalyzed transfer hydrogenation, see: Zassinovich G., Mestroni G., Gladiali S. Chem. Rev. 92:1992;1051 Bäckvall J.-E., Chowdhury R.L., Karlsson U., Wang G. Williams A.F., Floriani C., Merbach A.E. Perspectives in Coordination Chemistry. 1992;463-486 VCH, New York, Noyori R., Hashiguchi S. Acc. Chem. Res. 30:1997;97 Naota T., Takaya H., Murahashi S.-I. Chem. Rev. 98:1998;2599 Palmer M., Wills M. Tetrahedron: Asymmetry. 10:1999;2045.
35. Cho C.S., Kim B.T., Kim H.-S., Kim T.-J., Shim S.C. Organometallics. 22:2003;3608.
36. 2 generated in the initial oxidation stages by reducing 1-dodecene to dodecane (see Scheme 2).
37. It is also known that strong bases are used as cocatalysts to promote transition metal-catalyzed transfer hydrogenation. However, in the present reaction, KOH seems to act as a base for aldol reaction as well as a promotor for transfer hydrogenation.
38. In contrast to this result, the molar ratio [ketones]/[ 1 ] in oxidative cyclization of 1 with ketones (Ref. 7) was critical for the effective formation of quinolines since superfluous ketones are partially consumed by transfer hydrogenation of ketones by 1.
39. Cho C.S., Kim B.T., Lee M.J., Kim T.-J., Shim S.C. Angew. Chem., Int. Ed. 40:2001;958.
40. Palucki M., Buchwald S.L. J. Am. Chem. Soc. 119:1997;11108 Hamann B.C., Hartwig J.F. J. Am. Chem. Soc. 119:1997;12382.
41. Palucki M., Buchwald S.L. J. Am. Chem. Soc. 119:1997;11108 Hamann B.C., Hartwig J.F. J. Am. Chem. Soc. 119:1997;12382.
42. Tsuji Y., Nishimura H., Huh K.-T., Watanabe Y. J. Organomet. Chem. 286:1985;C44 Larock R.C., Kuo M. Tetrahedron Lett. 32:1991;569.
43. Tsuji Y., Nishimura H., Huh K.-T., Watanabe Y. J. Organomet. Chem. 286:1985;C44 Larock R.C., Kuo M. Tetrahedron Lett. 32:1991;569.
44. Hallman P.S., Stephenson T.A., Wilkinson G. Inorg. Synth. 12:1970;237.
45. Wiebe J.M., Caillé A.S., Trimble L., Lau C.K. Tetrahedron. 52:1996;11705.
46. Egi M., Liebeskind L.S. Org. Lett. 5:2003;801.
47. Cacchi S., Fabrizi G., Marinelli F. Synlett. 1999;401.
48. Mahanty J.S., De M., Das P., Kundu N.G. Tetrahedron. 53:1997;13397.
49. Cenini S., Bettettini E., Fedele M., Tollari S. J. Mol. Catal. A: Chem. 111:1996;37.
50. Furukawa N., Shibutani T., Fujihara H. Tetrahedron Lett. 28:1987;5845.
51. Fürstner A., Leitner A., Méndez M., Krause H. J. Am. Chem. Soc. 124:2002;13856.
52. Brown B.R., Hammick D.L., Newbould J., Price A.L. J. Chem. Soc. 1959;1311.
53. Ciufolini M.A., Mitchell J.W., Roschangar F. Tetrahedron Lett. 37:1996;8281.
54. Avramoff M., Sprinzak Y. J. Am. Chem. Soc. 78:1956;4090.
55. Fakhfakh M.A., Franck X., Fournet A., Hocquemiller R., Figadère B. Tetrahedron Lett. 42:2001;3847.
56. Schöpf C., Lehmann G. Justus Liebigs Ann. Chem. 497:1932;7.
57. Dzhemilev U.M., Selimov F.A., Khusnutdinov R.A. Akad. Nauk S. S. S. R. 1990;2447.
58. Curran D.P., Liu H. J. Am. Chem. Soc. 113:1991;2127.
59. Bell V.L., Cromwell N.H. J. Org. Chem. 23:1958;789.