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Volumn 62, Issue 14, 1997, Pages 4584-4590

Stereocontrolled Synthesis of Cyclic Ethers by Intramolecular Hetero-Michael Addition. 6. A Computational Study of the Annelation to 2,3-Disubstituted Tetrahydropyrans

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROPYRAN DERIVATIVE;

EID: 0030852861     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961925t     Document Type: Article
Times cited : (50)

References (73)
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    • ( 6) For intramolecular hetero-Michael additions used in the synthesis of tetrahydropyrans, see: (a) Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44. (b) Seebach, D.; Pohmakotr, M. Helv. Chim. Acta 1979, 62, 843. (c) Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. J. Am. Chem. Soc. 1980, 102, 6577. (d) Bates, H. A.; Deng, P.-N. J. Org. Chem. 1983, 48, 4479. (e) Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1989, 54, 1157. (f) Allevi, P.; Ciuffreda, P.; Colombo, D.; Monti, D.; Speranza, G.; Manitto, P. J. Chem. Soc., Perkin Trans. 1, 1989, 1281. (g) Kim, S.; Salomon, R. G. Tetrahedron Lett. 1989, 30, 6279. (h) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682. (i). Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888. (j) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Scola, P. M. Tetrahedron Lett. 1992, 33, 1549. (k) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739. (1) Dheilly, L.; Lièvre, C.; Fréehou, C.; Demailly, G. Tetrahedron Lett. 1993, 34, 5895. (m) Horita, K.; Hachiya, S.; Nagasawa, M., Hikota, M.; Yonemitsu, O. Synlett 1994, 38. (n) Roedern, E. G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 687.
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    • ( 6) For intramolecular hetero-Michael additions used in the synthesis of tetrahydropyrans, see: (a) Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44. (b) Seebach, D.; Pohmakotr, M. Helv. Chim. Acta 1979, 62, 843. (c) Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. J. Am. Chem. Soc. 1980, 102, 6577. (d) Bates, H. A.; Deng, P.-N. J. Org. Chem. 1983, 48, 4479. (e) Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1989, 54, 1157. (f) Allevi, P.; Ciuffreda, P.; Colombo, D.; Monti, D.; Speranza, G.; Manitto, P. J. Chem. Soc., Perkin Trans. 1, 1989, 1281. (g) Kim, S.; Salomon, R. G. Tetrahedron Lett. 1989, 30, 6279. (h) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682. (i). Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888. (j) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Scola, P. M. Tetrahedron Lett. 1992, 33, 1549. (k) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739. (1) Dheilly, L.; Lièvre, C.; Fréehou, C.; Demailly, G. Tetrahedron Lett. 1993, 34, 5895. (m) Horita, K.; Hachiya, S.; Nagasawa, M., Hikota, M.; Yonemitsu, O. Synlett 1994, 38. (n) Roedern, E. G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 687.
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    • Kim, S.1    Salomon, R.G.2
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    • ( 6) For intramolecular hetero-Michael additions used in the synthesis of tetrahydropyrans, see: (a) Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44. (b) Seebach, D.; Pohmakotr, M. Helv. Chim. Acta 1979, 62, 843. (c) Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. J. Am. Chem. Soc. 1980, 102, 6577. (d) Bates, H. A.; Deng, P.-N. J. Org. Chem. 1983, 48, 4479. (e) Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1989, 54, 1157. (f) Allevi, P.; Ciuffreda, P.; Colombo, D.; Monti, D.; Speranza, G.; Manitto, P. J. Chem. Soc., Perkin Trans. 1, 1989, 1281. (g) Kim, S.; Salomon, R. G. Tetrahedron Lett. 1989, 30, 6279. (h) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682. (i). Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888. (j) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Scola, P. M. Tetrahedron Lett. 1992, 33, 1549. (k) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739. (1) Dheilly, L.; Lièvre, C.; Fréehou, C.; Demailly, G. Tetrahedron Lett. 1993, 34, 5895. (m) Horita, K.; Hachiya, S.; Nagasawa, M., Hikota, M.; Yonemitsu, O. Synlett 1994, 38. (n) Roedern, E. G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 687.
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    • Nicolaou, K.C.1    Hwang, C.-K.2    Duggan, M.E.3
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    • ( 6) For intramolecular hetero-Michael additions used in the synthesis of tetrahydropyrans, see: (a) Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44. (b) Seebach, D.; Pohmakotr, M. Helv. Chim. Acta 1979, 62, 843. (c) Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. J. Am. Chem. Soc. 1980, 102, 6577. (d) Bates, H. A.; Deng, P.-N. J. Org. Chem. 1983, 48, 4479. (e) Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1989, 54, 1157. (f) Allevi, P.; Ciuffreda, P.; Colombo, D.; Monti, D.; Speranza, G.; Manitto, P. J. Chem. Soc., Perkin Trans. 1, 1989, 1281. (g) Kim, S.; Salomon, R. G. Tetrahedron Lett. 1989, 30, 6279. (h) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682. (i). Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888. (j) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Scola, P. M. Tetrahedron Lett. 1992, 33, 1549. (k) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739. (1) Dheilly, L.; Lièvre, C.; Fréehou, C.; Demailly, G. Tetrahedron Lett. 1993, 34, 5895. (m) Horita, K.; Hachiya, S.; Nagasawa, M., Hikota, M.; Yonemitsu, O. Synlett 1994, 38. (n) Roedern, E. G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 687.
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    • ( 6) For intramolecular hetero-Michael additions used in the synthesis of tetrahydropyrans, see: (a) Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44. (b) Seebach, D.; Pohmakotr, M. Helv. Chim. Acta 1979, 62, 843. (c) Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. J. Am. Chem. Soc. 1980, 102, 6577. (d) Bates, H. A.; Deng, P.-N. J. Org. Chem. 1983, 48, 4479. (e) Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1989, 54, 1157. (f) Allevi, P.; Ciuffreda, P.; Colombo, D.; Monti, D.; Speranza, G.; Manitto, P. J. Chem. Soc., Perkin Trans. 1, 1989, 1281. (g) Kim, S.; Salomon, R. G. Tetrahedron Lett. 1989, 30, 6279. (h) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682. (i). Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888. (j) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Scola, P. M. Tetrahedron Lett. 1992, 33, 1549. (k) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739. (1) Dheilly, L.; Lièvre, C.; Fréehou, C.; Demailly, G. Tetrahedron Lett. 1993, 34, 5895. (m) Horita, K.; Hachiya, S.; Nagasawa, M., Hikota, M.; Yonemitsu, O. Synlett 1994, 38. (n) Roedern, E. G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 687.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1549
    • Aicher, T.D.1    Buszek, K.R.2    Fang, F.G.3    Forsyth, C.J.4    Jung, S.H.5    Kishi, Y.6    Scola, P.M.7
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    • ( 6) For intramolecular hetero-Michael additions used in the synthesis of tetrahydropyrans, see: (a) Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44. (b) Seebach, D.; Pohmakotr, M. Helv. Chim. Acta 1979, 62, 843. (c) Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. J. Am. Chem. Soc. 1980, 102, 6577. (d) Bates, H. A.; Deng, P.-N. J. Org. Chem. 1983, 48, 4479. (e) Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1989, 54, 1157. (f) Allevi, P.; Ciuffreda, P.; Colombo, D.; Monti, D.; Speranza, G.; Manitto, P. J. Chem. Soc., Perkin Trans. 1, 1989, 1281. (g) Kim, S.; Salomon, R. G. Tetrahedron Lett. 1989, 30, 6279. (h) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682. (i). Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888. (j) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Scola, P. M. Tetrahedron Lett. 1992, 33, 1549. (k) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739. (1) Dheilly, L.; Lièvre, C.; Fréehou, C.; Demailly, G. Tetrahedron Lett. 1993, 34, 5895. (m) Horita, K.; Hachiya, S.; Nagasawa, M., Hikota, M.; Yonemitsu, O. Synlett 1994, 38. (n) Roedern, E. G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 687.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5739
    • Machinaga, N.1    Kibayashi, C.2
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    • ( 6) For intramolecular hetero-Michael additions used in the synthesis of tetrahydropyrans, see: (a) Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44. (b) Seebach, D.; Pohmakotr, M. Helv. Chim. Acta 1979, 62, 843. (c) Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. J. Am. Chem. Soc. 1980, 102, 6577. (d) Bates, H. A.; Deng, P.-N. J. Org. Chem. 1983, 48, 4479. (e) Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1989, 54, 1157. (f) Allevi, P.; Ciuffreda, P.; Colombo, D.; Monti, D.; Speranza, G.; Manitto, P. J. Chem. Soc., Perkin Trans. 1, 1989, 1281. (g) Kim, S.; Salomon, R. G. Tetrahedron Lett. 1989, 30, 6279. (h) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682. (i). Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888. (j) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Scola, P. M. Tetrahedron Lett. 1992, 33, 1549. (k) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739. (1) Dheilly, L.; Lièvre, C.; Fréehou, C.; Demailly, G. Tetrahedron Lett. 1993, 34, 5895. (m) Horita, K.; Hachiya, S.; Nagasawa, M., Hikota, M.; Yonemitsu, O. Synlett 1994, 38. (n) Roedern, E. G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 687.
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    • Dheilly, L.1    Lièvre, C.2    Fréehou, C.3    Demailly, G.4
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    • ( 6) For intramolecular hetero-Michael additions used in the synthesis of tetrahydropyrans, see: (a) Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44. (b) Seebach, D.; Pohmakotr, M. Helv. Chim. Acta 1979, 62, 843. (c) Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. J. Am. Chem. Soc. 1980, 102, 6577. (d) Bates, H. A.; Deng, P.-N. J. Org. Chem. 1983, 48, 4479. (e) Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1989, 54, 1157. (f) Allevi, P.; Ciuffreda, P.; Colombo, D.; Monti, D.; Speranza, G.; Manitto, P. J. Chem. Soc., Perkin Trans. 1, 1989, 1281. (g) Kim, S.; Salomon, R. G. Tetrahedron Lett. 1989, 30, 6279. (h) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682. (i). Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888. (j) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Scola, P. M. Tetrahedron Lett. 1992, 33, 1549. (k) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739. (1) Dheilly, L.; Lièvre, C.; Fréehou, C.; Demailly, G. Tetrahedron Lett. 1993, 34, 5895. (m) Horita, K.; Hachiya, S.; Nagasawa, M., Hikota, M.; Yonemitsu, O. Synlett 1994, 38. (n) Roedern, E. G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 687.
    • (1994) Synlett , pp. 38
    • Horita, K.1    Hachiya, S.2    Hikota M, N.M.3    Yonemitsu, O.4
  • 34
    • 33749666016 scopus 로고
    • ( 6) For intramolecular hetero-Michael additions used in the synthesis of tetrahydropyrans, see: (a) Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44. (b) Seebach, D.; Pohmakotr, M. Helv. Chim. Acta 1979, 62, 843. (c) Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. J. Am. Chem. Soc. 1980, 102, 6577. (d) Bates, H. A.; Deng, P.-N. J. Org. Chem. 1983, 48, 4479. (e) Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1989, 54, 1157. (f) Allevi, P.; Ciuffreda, P.; Colombo, D.; Monti, D.; Speranza, G.; Manitto, P. J. Chem. Soc., Perkin Trans. 1, 1989, 1281. (g) Kim, S.; Salomon, R. G. Tetrahedron Lett. 1989, 30, 6279. (h) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682. (i). Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888. (j) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Scola, P. M. Tetrahedron Lett. 1992, 33, 1549. (k) Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739. (1) Dheilly, L.; Lièvre, C.; Fréehou, C.; Demailly, G. Tetrahedron Lett. 1993, 34, 5895. (m) Horita, K.; Hachiya, S.; Nagasawa, M., Hikota, M.; Yonemitsu, O. Synlett 1994, 38. (n) Roedern, E. G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 687.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 687
    • Roedern, E.G.1    Kessler, H.2
  • 46
    • 85033135619 scopus 로고    scopus 로고
    • note
    • Semiempirical calculations using MOPAC/AM1 for the four possible enolates obtained in the cyclization, without countercation, in accordance with the criterion outlined in Figure 1 showed the following heats of formation: ec-ax (-160.88 kcal/mol), ax-ec (-160.95 kcal/mol), ec-ec (-161.14 kcal/mol), and ax-ax (-164.47 kcal/mol).
  • 49
    • 1542585811 scopus 로고
    • Since sodium parametrization is not available, a "sparkles" entity was used, considering its definition as a simplified atom of nuclear charge of + 1, ionic radius of 0.7 Å, and zero heat of formation, no orbitals and no ionization potential. Stewart, J. J. P. MOPAC Manual, 1990.
    • (1990) OPAC Manual
    • Stewart, J.J.P.M.1
  • 57
    • 0001651476 scopus 로고
    • The Z conformation is also the preferred one for the free enolates obtained from saturated esters: (a) Wang, X.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 1870. (b) Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1988, 110, 1872.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1870
    • Wang, X.1    Houk, K.N.2
  • 58
    • 33845278614 scopus 로고
    • The Z conformation is also the preferred one for the free enolates obtained from saturated esters: (a) Wang, X.; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 1870. (b) Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1988, 110, 1872.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1872
    • Wiberg, K.B.1    Laidig, K.E.2
  • 61
    • 85033146406 scopus 로고    scopus 로고
    • Unpublished results
    • (b) Thiel, W.; Clark, T. Unpublished results.
    • Thiel, W.1    Clark, T.2
  • 68
    • 85033136594 scopus 로고    scopus 로고
    • Calibration of the obtained results was performed using the higher basis set level 6-31+G*. Reference 24
    • Calibration of the obtained results was performed using the higher basis set level 6-31+G*. Reference 24.
  • 72
    • 85033149191 scopus 로고    scopus 로고
    • 3-21G//3-21G total energy of structures of Figure 6 in hartree: (a) -1149.707 41. (b) -1149.755 68. (c) -1149.737 05
    • 3-21G//3-21G total energy of structures of Figure 6 in hartree: (a) -1149.707 41. (b) -1149.755 68. (c) -1149.737 05.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.