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Volumn 51, Issue 1, 1998, Pages 9-18

Intramolecular Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double-bond geometry in controlling the diastereoselectivity of cyclizations teading to 2,6-disubstituted tetrahydropyrans and piperidines

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EID: 0002709948     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/C97173     Document Type: Article
Times cited : (31)

References (61)
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    • Seebach, D., and Pohmakotr, M., Helv. Chim. Acta, 1979, 62, 843; Seebach, D., Pohmakotr, M., Schregenberger, C., Weidmann, B., Mali, R. S., and Pohmakotr, S., Helv. Chim. Acta, 1982, 65, 419; Kim, Y., and Mundy, B. R, J. Org. Chem., 1982, 47, 3556; Ley, S. V., Lygo, B., Molines, H., and Morton, J. A., J. Chem. Soc., Chem. Commun., 1982, 1251; Masaki, Y., Serizawa, Y., Nagata, K., and Kaji, K., Chem. Lett., 1983, 1601; Bates, H. A., and Deng, P.-N., J. Org. Chem, 1983, 48, 4479; Lichtenthaler, F. W., Klinger, F. D., and Jarglis, P., Carbohydr. Res., 1984, 132, C1; Gallagher, T., J. Chem. Soc., Chem. Commun., 1984, 1554; Semmelhack, M. F., and Bodurow, C., J. Am. Chem. Soc., 1984, 106, 1496; Keinan, E., Seth, K. K., and Lamed, R., J. Am. Chem. Soc., 1986, 108, 3474; Nussbaumer, C., and Frater, G., Helv. Chim. Acta, 1987, 70, 396; Greenspoon, N., and Keinan, E., J. Org. Chem., 1988, 53, 3723; Coppi, L., Ricci, A., and Taddei, M., J. Org. Chem., 1988, 53, 911; Kotsuki, H., Ushio, Y., Kadota, I., and Ochi, M., Chem. Lett., 1988, 927; Wei, Z. Y., Wang, D., Li, J. S, and Chan, T. H., J. Org. Chem., 1989, 54, 5768; Homma, K., and Mukaiyama, T., Chem. Lett., 1989, 893; Kobayashi, K., and Suginome, H., Bull. Chem. Soc. Jpn, 1989, 62, 951; Ishihara, K., Mori, A., and Yamamoto, H., Tetrahedron, 1990, 46, 4595; Hansson, S., Miller, J. F., and Liebeskind, L. S., J. Am. Chem. Soc., 1990, 112, 9660; Ragoussis, V., and Theodorou, V., Synthesis, 1993, 84; Lee, E., Tae, J. S., Lee, C., and Park, C. M., Tetrahedron Lett., 1993, 34, 4831; Varelis, P., Graham, A. J., Johnson, B. L., Skelton, B. W., and White, A. H., Aust. J. Chem., 1994, 47, 1735; Muraoka, O., Okumura, M., Maeda, T., Wang, L, and Tanabe, G., Chem. Pharm. Bull., 1995, 43, 517.
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    • Seebach, D., and Pohmakotr, M., Helv. Chim. Acta, 1979, 62, 843; Seebach, D., Pohmakotr, M., Schregenberger, C., Weidmann, B., Mali, R. S., and Pohmakotr, S., Helv. Chim. Acta, 1982, 65, 419; Kim, Y., and Mundy, B. R, J. Org. Chem., 1982, 47, 3556; Ley, S. V., Lygo, B., Molines, H., and Morton, J. A., J. Chem. Soc., Chem. Commun., 1982, 1251; Masaki, Y., Serizawa, Y., Nagata, K., and Kaji, K., Chem. Lett., 1983, 1601; Bates, H. A., and Deng, P.-N., J. Org. Chem, 1983, 48, 4479; Lichtenthaler, F. W., Klinger, F. D., and Jarglis, P., Carbohydr. Res., 1984, 132, C1; Gallagher, T., J. Chem. Soc., Chem. Commun., 1984, 1554; Semmelhack, M. F., and Bodurow, C., J. Am. Chem. Soc., 1984, 106, 1496; Keinan, E., Seth, K. K., and Lamed, R., J. Am. Chem. Soc., 1986, 108, 3474; Nussbaumer, C., and Frater, G., Helv. Chim. Acta, 1987, 70, 396; Greenspoon, N., and Keinan, E., J. Org. Chem., 1988, 53, 3723; Coppi, L., Ricci, A., and Taddei, M., J. Org. Chem., 1988, 53, 911; Kotsuki, H., Ushio, Y., Kadota, I., and Ochi, M., Chem. Lett., 1988, 927; Wei, Z. Y., Wang, D., Li, J. S, and Chan, T. H., J. Org. Chem., 1989, 54, 5768; Homma, K., and Mukaiyama, T., Chem. Lett., 1989, 893; Kobayashi, K., and Suginome, H., Bull. Chem. Soc. Jpn, 1989, 62, 951; Ishihara, K., Mori, A., and Yamamoto, H., Tetrahedron, 1990, 46, 4595; Hansson, S., Miller, J. F., and Liebeskind, L. S., J. Am. Chem. Soc., 1990, 112, 9660; Ragoussis, V., and Theodorou, V., Synthesis, 1993, 84; Lee, E., Tae, J. S., Lee, C., and Park, C. M., Tetrahedron Lett., 1993, 34, 4831; Varelis, P., Graham, A. J., Johnson, B. L., Skelton, B. W., and White, A. H., Aust. J. Chem., 1994, 47, 1735; Muraoka, O., Okumura, M., Maeda, T., Wang, L, and Tanabe, G., Chem. Pharm. Bull., 1995, 43, 517.
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    • Seebach, D., and Pohmakotr, M., Helv. Chim. Acta, 1979, 62, 843; Seebach, D., Pohmakotr, M., Schregenberger, C., Weidmann, B., Mali, R. S., and Pohmakotr, S., Helv. Chim. Acta, 1982, 65, 419; Kim, Y., and Mundy, B. R, J. Org. Chem., 1982, 47, 3556; Ley, S. V., Lygo, B., Molines, H., and Morton, J. A., J. Chem. Soc., Chem. Commun., 1982, 1251; Masaki, Y., Serizawa, Y., Nagata, K., and Kaji, K., Chem. Lett., 1983, 1601; Bates, H. A., and Deng, P.-N., J. Org. Chem, 1983, 48, 4479; Lichtenthaler, F. W., Klinger, F. D., and Jarglis, P., Carbohydr. Res., 1984, 132, C1; Gallagher, T., J. Chem. Soc., Chem. Commun., 1984, 1554; Semmelhack, M. F., and Bodurow, C., J. Am. Chem. Soc., 1984, 106, 1496; Keinan, E., Seth, K. K., and Lamed, R., J. Am. Chem. Soc., 1986, 108, 3474; Nussbaumer, C., and Frater, G., Helv. Chim. Acta, 1987, 70, 396; Greenspoon, N., and Keinan, E., J. Org. Chem., 1988, 53, 3723; Coppi, L., Ricci, A., and Taddei, M., J. Org. Chem., 1988, 53, 911; Kotsuki, H., Ushio, Y., Kadota, I., and Ochi, M., Chem. Lett., 1988, 927; Wei, Z. Y., Wang, D., Li, J. S, and Chan, T. H., J. Org. Chem., 1989, 54, 5768; Homma, K., and Mukaiyama, T., Chem. Lett., 1989, 893; Kobayashi, K., and Suginome, H., Bull. Chem. Soc. Jpn, 1989, 62, 951; Ishihara, K., Mori, A., and Yamamoto, H., Tetrahedron, 1990, 46, 4595; Hansson, S., Miller, J. F., and Liebeskind, L. S., J. Am. Chem. Soc., 1990, 112, 9660; Ragoussis, V., and Theodorou, V., Synthesis, 1993, 84; Lee, E., Tae, J. S., Lee, C., and Park, C. M., Tetrahedron Lett., 1993, 34, 4831; Varelis, P., Graham, A. J., Johnson, B. L., Skelton, B. W., and White, A. H., Aust. J. Chem., 1994, 47, 1735; Muraoka, O., Okumura, M., Maeda, T., Wang, L, and Tanabe, G., Chem. Pharm. Bull., 1995, 43, 517.
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    • Seebach, D., and Pohmakotr, M., Helv. Chim. Acta, 1979, 62, 843; Seebach, D., Pohmakotr, M., Schregenberger, C., Weidmann, B., Mali, R. S., and Pohmakotr, S., Helv. Chim. Acta, 1982, 65, 419; Kim, Y., and Mundy, B. R, J. Org. Chem., 1982, 47, 3556; Ley, S. V., Lygo, B., Molines, H., and Morton, J. A., J. Chem. Soc., Chem. Commun., 1982, 1251; Masaki, Y., Serizawa, Y., Nagata, K., and Kaji, K., Chem. Lett., 1983, 1601; Bates, H. A., and Deng, P.-N., J. Org. Chem, 1983, 48, 4479; Lichtenthaler, F. W., Klinger, F. D., and Jarglis, P., Carbohydr. Res., 1984, 132, C1; Gallagher, T., J. Chem. Soc., Chem. Commun., 1984, 1554; Semmelhack, M. F., and Bodurow, C., J. Am. Chem. Soc., 1984, 106, 1496; Keinan, E., Seth, K. K., and Lamed, R., J. Am. Chem. Soc., 1986, 108, 3474; Nussbaumer, C., and Frater, G., Helv. Chim. Acta, 1987, 70, 396; Greenspoon, N., and Keinan, E., J. Org. Chem., 1988, 53, 3723; Coppi, L., Ricci, A., and Taddei, M., J. Org. Chem., 1988, 53, 911; Kotsuki, H., Ushio, Y., Kadota, I., and Ochi, M., Chem. Lett., 1988, 927; Wei, Z. Y., Wang, D., Li, J. S, and Chan, T. H., J. Org. Chem., 1989, 54, 5768; Homma, K., and Mukaiyama, T., Chem. Lett., 1989, 893; Kobayashi, K., and Suginome, H., Bull. Chem. Soc. Jpn, 1989, 62, 951; Ishihara, K., Mori, A., and Yamamoto, H., Tetrahedron, 1990, 46, 4595; Hansson, S., Miller, J. F., and Liebeskind, L. S., J. Am. Chem. Soc., 1990, 112, 9660; Ragoussis, V., and Theodorou, V., Synthesis, 1993, 84; Lee, E., Tae, J. S., Lee, C., and Park, C. M., Tetrahedron Lett., 1993, 34, 4831; Varelis, P., Graham, A. J., Johnson, B. L., Skelton, B. W., and White, A. H., Aust. J. Chem., 1994, 47, 1735; Muraoka, O., Okumura, M., Maeda, T., Wang, L, and Tanabe, G., Chem. Pharm. Bull., 1995, 43, 517.
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