메뉴 건너뛰기




Volumn 7, Issue 4, 1999, Pages 519-528

Optical resolution of chirally functionalized [60]fullerene through formation of diastereomeric methoxyphenylacetic acid esters

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; ESTERS; GEL PERMEATION CHROMATOGRAPHY; HIGH PRESSURE LIQUID CHROMATOGRAPHY; OPTICAL RESOLVING POWER; SILICA GEL;

EID: 0032599615     PISSN: 1064122X     EISSN: None     Source Type: Journal    
DOI: 10.1080/10641229909351358     Document Type: Article
Times cited : (7)

References (29)
  • 1
    • 0029809466 scopus 로고    scopus 로고
    • Nakamura, E., Tokuyama, H., Yamago, S., Shiraki, T., Sugiura, Y., Bull. Soc. Chem. Jpn., 1996, 69, 2143. K. Irie, K., Nakamura, Y., Ohigashi, H., Tokuyama, H., Yamago, S., Nakamura, E., Biosci. Biotech. Biochem., 1996, 60, 1359. Tokuyama, H., Yamago, S., Nakamura, E., Shiraki T., Sugiura, Y., J. Am. Chem. Soc., 1993, 115, 7918. Yamago, S., Tokuyama, H., Nakamura, E., Kikuchi, K., Kananishi, S., Sueki, K., Nakahara, H., Enomoto, S., Ambe, F., Chem. Biol. 1995, 2, 385. Boutorine, A. S., Tokuyama, H., Takasugi, M., Isobe, H., Nakamura E., Hèléne, C., Angew. Chem. Int. Ed. Engl., 1994, 33, 2462. An, Y. Z., Chen, C. H. B., Anderson, J. L., Sigman, D. S., Foote, C. S., Rubin, Y. Tetrahedron, 1996, 52, 5179. Friedman, S. H., Decamp, D. L., Sijbesma, R. P., Srdanov, G., Wudl, F., Kenyon, G. L., J. Am. Chem. Soc., 1993, 115, 6506. Schinazi, R. F., Sijbesma, R., Srdanov, G., Hill, C. L., Wudl, F. Antimicrob. Agents Chemother. 1993, 37, 1707.
    • (1996) Bull. Soc. Chem. Jpn. , vol.69 , pp. 2143
    • Nakamura, E.1    Tokuyama, H.2    Yamago, S.3    Shiraki, T.4    Sugiura, Y.5
  • 2
    • 0030221555 scopus 로고    scopus 로고
    • Nakamura, E., Tokuyama, H., Yamago, S., Shiraki, T., Sugiura, Y., Bull. Soc. Chem. Jpn., 1996, 69, 2143. K. Irie, K., Nakamura, Y., Ohigashi, H., Tokuyama, H., Yamago, S., Nakamura, E., Biosci. Biotech. Biochem., 1996, 60, 1359. Tokuyama, H., Yamago, S., Nakamura, E., Shiraki T., Sugiura, Y., J. Am. Chem. Soc., 1993, 115, 7918. Yamago, S., Tokuyama, H., Nakamura, E., Kikuchi, K., Kananishi, S., Sueki, K., Nakahara, H., Enomoto, S., Ambe, F., Chem. Biol. 1995, 2, 385. Boutorine, A. S., Tokuyama, H., Takasugi, M., Isobe, H., Nakamura E., Hèléne, C., Angew. Chem. Int. Ed. Engl., 1994, 33, 2462. An, Y. Z., Chen, C. H. B., Anderson, J. L., Sigman, D. S., Foote, C. S., Rubin, Y. Tetrahedron, 1996, 52, 5179. Friedman, S. H., Decamp, D. L., Sijbesma, R. P., Srdanov, G., Wudl, F., Kenyon, G. L., J. Am. Chem. Soc., 1993, 115, 6506. Schinazi, R. F., Sijbesma, R., Srdanov, G., Hill, C. L., Wudl, F. Antimicrob. Agents Chemother. 1993, 37, 1707.
    • (1996) Biosci. Biotech. Biochem. , vol.60 , pp. 1359
    • Irie, K.1    Nakamura, Y.2    Ohigashi, H.3    Tokuyama, H.4    Yamago, S.5    Nakamura, E.6
  • 3
    • 0027486864 scopus 로고
    • Nakamura, E., Tokuyama, H., Yamago, S., Shiraki, T., Sugiura, Y., Bull. Soc. Chem. Jpn., 1996, 69, 2143. K. Irie, K., Nakamura, Y., Ohigashi, H., Tokuyama, H., Yamago, S., Nakamura, E., Biosci. Biotech. Biochem., 1996, 60, 1359. Tokuyama, H., Yamago, S., Nakamura, E., Shiraki T., Sugiura, Y., J. Am. Chem. Soc., 1993, 115, 7918. Yamago, S., Tokuyama, H., Nakamura, E., Kikuchi, K., Kananishi, S., Sueki, K., Nakahara, H., Enomoto, S., Ambe, F., Chem. Biol. 1995, 2, 385. Boutorine, A. S., Tokuyama, H., Takasugi, M., Isobe, H., Nakamura E., Hèléne, C., Angew. Chem. Int. Ed. Engl., 1994, 33, 2462. An, Y. Z., Chen, C. H. B., Anderson, J. L., Sigman, D. S., Foote, C. S., Rubin, Y. Tetrahedron, 1996, 52, 5179. Friedman, S. H., Decamp, D. L., Sijbesma, R. P., Srdanov, G., Wudl, F., Kenyon, G. L., J. Am. Chem. Soc., 1993, 115, 6506. Schinazi, R. F., Sijbesma, R., Srdanov, G., Hill, C. L., Wudl, F. Antimicrob. Agents Chemother. 1993, 37, 1707.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7918
    • Tokuyama, H.1    Yamago, S.2    Nakamura, E.3    Shiraki, T.4    Sugiura, Y.5
  • 4
    • 0029311495 scopus 로고
    • Nakamura, E., Tokuyama, H., Yamago, S., Shiraki, T., Sugiura, Y., Bull. Soc. Chem. Jpn., 1996, 69, 2143. K. Irie, K., Nakamura, Y., Ohigashi, H., Tokuyama, H., Yamago, S., Nakamura, E., Biosci. Biotech. Biochem., 1996, 60, 1359. Tokuyama, H., Yamago, S., Nakamura, E., Shiraki T., Sugiura, Y., J. Am. Chem. Soc., 1993, 115, 7918. Yamago, S., Tokuyama, H., Nakamura, E., Kikuchi, K., Kananishi, S., Sueki, K., Nakahara, H., Enomoto, S., Ambe, F., Chem. Biol. 1995, 2, 385. Boutorine, A. S., Tokuyama, H., Takasugi, M., Isobe, H., Nakamura E., Hèléne, C., Angew. Chem. Int. Ed. Engl., 1994, 33, 2462. An, Y. Z., Chen, C. H. B., Anderson, J. L., Sigman, D. S., Foote, C. S., Rubin, Y. Tetrahedron, 1996, 52, 5179. Friedman, S. H., Decamp, D. L., Sijbesma, R. P., Srdanov, G., Wudl, F., Kenyon, G. L., J. Am. Chem. Soc., 1993, 115, 6506. Schinazi, R. F., Sijbesma, R., Srdanov, G., Hill, C. L., Wudl, F. Antimicrob. Agents Chemother. 1993, 37, 1707.
    • (1995) Chem. Biol. , vol.2 , pp. 385
    • Yamago, S.1    Tokuyama, H.2    Nakamura, E.3    Kikuchi, K.4    Kananishi, S.5    Sueki, K.6    Nakahara, H.7    Enomoto, S.8    Ambe, F.9
  • 5
    • 33751134818 scopus 로고
    • Nakamura, E., Tokuyama, H., Yamago, S., Shiraki, T., Sugiura, Y., Bull. Soc. Chem. Jpn., 1996, 69, 2143. K. Irie, K., Nakamura, Y., Ohigashi, H., Tokuyama, H., Yamago, S., Nakamura, E., Biosci. Biotech. Biochem., 1996, 60, 1359. Tokuyama, H., Yamago, S., Nakamura, E., Shiraki T., Sugiura, Y., J. Am. Chem. Soc., 1993, 115, 7918. Yamago, S., Tokuyama, H., Nakamura, E., Kikuchi, K., Kananishi, S., Sueki, K., Nakahara, H., Enomoto, S., Ambe, F., Chem. Biol. 1995, 2, 385. Boutorine, A. S., Tokuyama, H., Takasugi, M., Isobe, H., Nakamura E., Hèléne, C., Angew. Chem. Int. Ed. Engl., 1994, 33, 2462. An, Y. Z., Chen, C. H. B., Anderson, J. L., Sigman, D. S., Foote, C. S., Rubin, Y. Tetrahedron, 1996, 52, 5179. Friedman, S. H., Decamp, D. L., Sijbesma, R. P., Srdanov, G., Wudl, F., Kenyon, G. L., J. Am. Chem. Soc., 1993, 115, 6506. Schinazi, R. F., Sijbesma, R., Srdanov, G., Hill, C. L., Wudl, F. Antimicrob. Agents Chemother. 1993, 37, 1707.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2462
    • Boutorine, A.S.1    Tokuyama, H.2    Takasugi, M.3    Isobe, H.4    Nakamura, E.5    Hèléne, C.6
  • 6
    • 0029961154 scopus 로고    scopus 로고
    • Nakamura, E., Tokuyama, H., Yamago, S., Shiraki, T., Sugiura, Y., Bull. Soc. Chem. Jpn., 1996, 69, 2143. K. Irie, K., Nakamura, Y., Ohigashi, H., Tokuyama, H., Yamago, S., Nakamura, E., Biosci. Biotech. Biochem., 1996, 60, 1359. Tokuyama, H., Yamago, S., Nakamura, E., Shiraki T., Sugiura, Y., J. Am. Chem. Soc., 1993, 115, 7918. Yamago, S., Tokuyama, H., Nakamura, E., Kikuchi, K., Kananishi, S., Sueki, K., Nakahara, H., Enomoto, S., Ambe, F., Chem. Biol. 1995, 2, 385. Boutorine, A. S., Tokuyama, H., Takasugi, M., Isobe, H., Nakamura E., Hèléne, C., Angew. Chem. Int. Ed. Engl., 1994, 33, 2462. An, Y. Z., Chen, C. H. B., Anderson, J. L., Sigman, D. S., Foote, C. S., Rubin, Y. Tetrahedron, 1996, 52, 5179. Friedman, S. H., Decamp, D. L., Sijbesma, R. P., Srdanov, G., Wudl, F., Kenyon, G. L., J. Am. Chem. Soc., 1993, 115, 6506. Schinazi, R. F., Sijbesma, R., Srdanov, G., Hill, C. L., Wudl, F. Antimicrob. Agents Chemother. 1993, 37, 1707.
    • (1996) Tetrahedron , vol.52 , pp. 5179
    • An, Y.Z.1    Chen, C.H.B.2    Anderson, J.L.3    Sigman, D.S.4    Foote, C.S.5    Rubin, Y.6
  • 7
    • 0027244713 scopus 로고
    • Nakamura, E., Tokuyama, H., Yamago, S., Shiraki, T., Sugiura, Y., Bull. Soc. Chem. Jpn., 1996, 69, 2143. K. Irie, K., Nakamura, Y., Ohigashi, H., Tokuyama, H., Yamago, S., Nakamura, E., Biosci. Biotech. Biochem., 1996, 60, 1359. Tokuyama, H., Yamago, S., Nakamura, E., Shiraki T., Sugiura, Y., J. Am. Chem. Soc., 1993, 115, 7918. Yamago, S., Tokuyama, H., Nakamura, E., Kikuchi, K., Kananishi, S., Sueki, K., Nakahara, H., Enomoto, S., Ambe, F., Chem. Biol. 1995, 2, 385. Boutorine, A. S., Tokuyama, H., Takasugi, M., Isobe, H., Nakamura E., Hèléne, C., Angew. Chem. Int. Ed. Engl., 1994, 33, 2462. An, Y. Z., Chen, C. H. B., Anderson, J. L., Sigman, D. S., Foote, C. S., Rubin, Y. Tetrahedron, 1996, 52, 5179. Friedman, S. H., Decamp, D. L., Sijbesma, R. P., Srdanov, G., Wudl, F., Kenyon, G. L., J. Am. Chem. Soc., 1993, 115, 6506. Schinazi, R. F., Sijbesma, R., Srdanov, G., Hill, C. L., Wudl, F. Antimicrob. Agents Chemother. 1993, 37, 1707.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 6506
    • Friedman, S.H.1    Decamp, D.L.2    Sijbesma, R.P.3    Srdanov, G.4    Wudl, F.5    Kenyon, G.L.6
  • 8
    • 0027255192 scopus 로고
    • Nakamura, E., Tokuyama, H., Yamago, S., Shiraki, T., Sugiura, Y., Bull. Soc. Chem. Jpn., 1996, 69, 2143. K. Irie, K., Nakamura, Y., Ohigashi, H., Tokuyama, H., Yamago, S., Nakamura, E., Biosci. Biotech. Biochem., 1996, 60, 1359. Tokuyama, H., Yamago, S., Nakamura, E., Shiraki T., Sugiura, Y., J. Am. Chem. Soc., 1993, 115, 7918. Yamago, S., Tokuyama, H., Nakamura, E., Kikuchi, K., Kananishi, S., Sueki, K., Nakahara, H., Enomoto, S., Ambe, F., Chem. Biol. 1995, 2, 385. Boutorine, A. S., Tokuyama, H., Takasugi, M., Isobe, H., Nakamura E., Hèléne, C., Angew. Chem. Int. Ed. Engl., 1994, 33, 2462. An, Y. Z., Chen, C. H. B., Anderson, J. L., Sigman, D. S., Foote, C. S., Rubin, Y. Tetrahedron, 1996, 52, 5179. Friedman, S. H., Decamp, D. L., Sijbesma, R. P., Srdanov, G., Wudl, F., Kenyon, G. L., J. Am. Chem. Soc., 1993, 115, 6506. Schinazi, R. F., Sijbesma, R., Srdanov, G., Hill, C. L., Wudl, F. Antimicrob. Agents Chemother. 1993, 37, 1707.
    • (1993) Antimicrob. Agents Chemother. , vol.37 , pp. 1707
    • Schinazi, R.F.1    Sijbesma, R.2    Srdanov, G.3    Hill, C.L.4    Wudl, F.5
  • 10
    • 0030005672 scopus 로고    scopus 로고
    • Yamago, S., Yanagawa M., Mukai, H., Nakamura, E. Tetrahedron, 1996, 52, 5091. Sawamura, M., Iikura, H., Nakamura, E., J. Am. Chem. Soc., 1996, 118, 12850. Iikura, H., Mori, S., Sawamura M., Nakamura, E. J. Org. Chem., 1997, 62, 7912. Sawamura, M., Iikura, H., Hirai, A., Nakamura, E., J. Am. Chem. Soc. 1998, 120, 8285.
    • (1996) Tetrahedron , vol.52 , pp. 5091
    • Yamago, S.1    Yanagawa, M.2    Mukai, H.3    Nakamura, E.4
  • 11
    • 0030475726 scopus 로고    scopus 로고
    • Yamago, S., Yanagawa M., Mukai, H., Nakamura, E. Tetrahedron, 1996, 52, 5091. Sawamura, M., Iikura, H., Nakamura, E., J. Am. Chem. Soc., 1996, 118, 12850. Iikura, H., Mori, S., Sawamura M., Nakamura, E. J. Org. Chem., 1997, 62, 7912. Sawamura, M., Iikura, H., Hirai, A., Nakamura, E., J. Am. Chem. Soc. 1998, 120, 8285.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 12850
    • Sawamura, M.1    Iikura, H.2    Nakamura, E.3
  • 12
    • 0000752260 scopus 로고    scopus 로고
    • Yamago, S., Yanagawa M., Mukai, H., Nakamura, E. Tetrahedron, 1996, 52, 5091. Sawamura, M., Iikura, H., Nakamura, E., J. Am. Chem. Soc., 1996, 118, 12850. Iikura, H., Mori, S., Sawamura M., Nakamura, E. J. Org. Chem., 1997, 62, 7912. Sawamura, M., Iikura, H., Hirai, A., Nakamura, E., J. Am. Chem. Soc. 1998, 120, 8285.
    • (1997) J. Org. Chem. , vol.62 , pp. 7912
    • Iikura, H.1    Mori, S.2    Sawamura, M.3    Nakamura, E.4
  • 13
    • 0032547266 scopus 로고    scopus 로고
    • Yamago, S., Yanagawa M., Mukai, H., Nakamura, E. Tetrahedron, 1996, 52, 5091. Sawamura, M., Iikura, H., Nakamura, E., J. Am. Chem. Soc., 1996, 118, 12850. Iikura, H., Mori, S., Sawamura M., Nakamura, E. J. Org. Chem., 1997, 62, 7912. Sawamura, M., Iikura, H., Hirai, A., Nakamura, E., J. Am. Chem. Soc. 1998, 120, 8285.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 8285
    • Sawamura, M.1    Iikura, H.2    Hirai, A.3    Nakamura, E.4
  • 15
    • 0031956896 scopus 로고    scopus 로고
    • Djojo, F., Hirsch, A. Chem. Eur. J., 1998, 4, 344; Schergna, S., Ros, T. D., Linda, P., Ebert, C., Gardossi, L., Prato, M. Tetrahedron Lett., 1998, 39, 7791.
    • (1998) Chem. Eur. J. , vol.4 , pp. 344
    • Djojo, F.1    Hirsch, A.2
  • 21
    • 0027495629 scopus 로고
    • Tokuyama, H., Nakamura, M., Nakamura, E., Tetrahedron Lett., 1993, 34, 7429. Tokuyama, H., Isobe, H., Nakamura, E., Bull. Chem. Soc., Jpn., 1995, 68, 935. Amano, H. Uekusa, H., Ohashi, Y., Tokuyama, H., Nakamura, E., Mol. Cryst. Liq. Cryst., 1996, 276, 291.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7429
    • Tokuyama, H.1    Nakamura, M.2    Nakamura, E.3
  • 22
    • 0027495629 scopus 로고
    • Tokuyama, H., Nakamura, M., Nakamura, E., Tetrahedron Lett., 1993, 34, 7429. Tokuyama, H., Isobe, H., Nakamura, E., Bull. Chem. Soc., Jpn., 1995, 68, 935. Amano, H. Uekusa, H., Ohashi, Y., Tokuyama, H., Nakamura, E., Mol. Cryst. Liq. Cryst., 1996, 276, 291.
    • (1995) Bull. Chem. Soc., Jpn. , vol.68 , pp. 935
    • Tokuyama, H.1    Isobe, H.2    Nakamura, E.3
  • 24
    • 0001400535 scopus 로고    scopus 로고
    • The specification of the absolute configuration of inherent chiral fullerenes: Thielgen, C., Herrman, A., Diederich, F., Helv. Chim. Acta, 1997, 80, 183. Thilgen, C., Herrman, A. Diederich, F., Angew. Chem. Int. Ed. Engl. 1997, 36, 2268.
    • (1997) Helv. Chim. Acta , vol.80 , pp. 183
    • Thielgen, C.1    Herrman, A.2    Diederich, F.3
  • 25
    • 0000825727 scopus 로고    scopus 로고
    • The specification of the absolute configuration of inherent chiral fullerenes: Thielgen, C., Herrman, A., Diederich, F., Helv. Chim. Acta, 1997, 80, 183. Thilgen, C., Herrman, A. Diederich, F., Angew. Chem. Int. Ed. Engl. 1997, 36, 2268.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2268
    • Thilgen, C.1    Herrman, A.2    Diederich, F.3
  • 26
    • 85038071045 scopus 로고    scopus 로고
    • note
    • f 0.38 and 0.36, 2% ethyl acetate in toluene).
  • 27
    • 85038070176 scopus 로고    scopus 로고
    • note
    • Deprotection of MPA under basic conditions was unsuccessful.
  • 28
    • 85038067973 scopus 로고    scopus 로고
    • note
    • 3, c=0.01)=-138).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.