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Volumn 107, Issue 5, 1985, Pages 1435-1437

Stereoelectronic Controlling Features of Allylic Asymmetry. Application to Ester Enolate Alkylations

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EID: 0042979182     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00291a067     Document Type: Article
Times cited : (126)

References (20)
  • 1
    • 0001399730 scopus 로고
    • For recent theoretical studies, see: (a) (b) Caramella, P.; Rondan, N. G.; Paddon-Row, N. M.; Houk, K. E. J. Am. Chem. Soc. 1981, 103, 2438. (c) Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162. (d) Houk, K. N. Pure Appl. Chem. 1983, 55, 277
    • For recent theoretical studies, see: (a) Ahn, N. T. Top. Curr. Chem. 1980, 88, 145. (b) Caramella, P.; Rondan, N. G.; Paddon-Row, N. M.; Houk, K. E. J. Am. Chem. Soc. 1981, 103, 2438. (c) Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162. (d) Houk, K. N. Pure Appl. Chem. 1983, 55, 277.
    • (1980) Top. Curr. Chem. , vol.88 , pp. 145
    • Ahn, N.T.1
  • 2
    • 0001707503 scopus 로고
    • For recent discussions on stereoselective electrophilic additions to olefins, see: (a) (b) Houk, K. N.; Moses, S. R.; Wu, Y.-D.; Rondan, N. G.; Jager, V.; Schohe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984, 106, 3880. (c) Houk, K. N.; Rondan, N. G.; Wu, Y.-D.; Metz, J. J.; Paddon-Row, M. N. Tetrahedron 1984, 40, 2257.
    • For recent discussions on stereoselective electrophilic additions to olefins, see: (a) Schreiber, S. L.; Satake, K. J. Am. Chem. Soc. 1983, 105, 6723. (b) Houk, K. N.; Moses, S. R.; Wu, Y.-D.; Rondan, N. G.; Jager, V.; Schohe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984, 106, 3880. (c) Houk, K. N.; Rondan, N. G.; Wu, Y.-D.; Metz, J. J.; Paddon-Row, M. N. Tetrahedron 1984, 40, 2257.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 6723
    • Schreiber, S.L.1    Satake, K.2
  • 4
    • 0003787137 scopus 로고
    • Frontier Orbitals and Organic Chemical Reactions
    • Wiley: New York (b) Epiotis, N. D.; Cherry, W. R.; Shaik, S.; Yates, R. L.; Bernardi, F. Top. Curr. Chem. 1977, 70, 1.
    • Fleming, I. “Frontier Orbitals and Organic Chemical Reactions”; Wiley: New York, 1977. (b) Epiotis, N. D.; Cherry, W. R.; Shaik, S.; Yates, R. L.; Bernardi, F. Top. Curr. Chem. 1977, 70, 1.
    • (1977)
    • Fleming, I.1
  • 5
    • 0000144488 scopus 로고
    • (b) Roush, W. R.; Lesur, B. M. Tetrahedron Lett. 1983, 2231. (c) Fronza, G.; Fuganti, C.; Graselli, P.; Majori, L.; Pedrocchi-Fantoni, G.; Spreafico, F. J. Org. Chem. 1982, 47, 3289. (d) Isobe, M.; Kitamura, M.; Goto, T. Tetrahedron Lett. 1980, 4727. (e) Dyong, I.; Bendlin, H. Chem. Ber. 1979, 112, 717
    • Matsunga, H.; Sakamaki, T.; Nagaoka, H.; Yamada, Y. Tetrahedron Lett. 1983, 3009. (b) Roush, W. R.; Lesur, B. M. Tetrahedron Lett. 1983, 2231. (c) Fronza, G.; Fuganti, C.; Graselli, P.; Majori, L.; Pedrocchi-Fantoni, G.; Spreafico, F. J. Org. Chem. 1982, 47, 3289. (d) Isobe, M.; Kitamura, M.; Goto, T. Tetrahedron Lett. 1980, 4727. (e) Dyong, I.; Bendlin, H. Chem. Ber. 1979, 112, 717.
    • (1983) Tetrahedron Lett , pp. 3009
    • Matsunga, H.1    Sakamaki, T.2    Nagaoka, H.3    Yamada, Y.4
  • 6
    • 0010382074 scopus 로고
    • For representative examples, see: (a) (b) Mulzer, J.; Angermarin, A. Tetrahedron Lett. 1983, 2843. (c) Roush, W. R.; Harris, D. J.; Lesur, B. M. Tetrahedron Lett. 1983, 2227. (d) Mukaiyama, T.; Yuki, Y.; Suzuki, K. Chem. Lett. 1982, 1169. (e) Mukaiyama, T.; Suzuki, K.; Yamada, T. Chem. Lett. 1982, 929. (f) Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pirrung, M. C.; White, C. T.; Van Derver, D. J. Org. Chem. 1980, 45, 3846
    • For representative examples, see: (a) Fuganti, C.; Grasselli, P.; Servi, S.; Spreafico, F.; Zirotti, C.; Casati, P. J. Chem. Res. 1984, 112. (b) Mulzer, J.; Angermarin, A. Tetrahedron Lett. 1983, 2843. (c) Roush, W. R.; Harris, D. J.; Lesur, B. M. Tetrahedron Lett. 1983, 2227. (d) Mukaiyama, T.; Yuki, Y.; Suzuki, K. Chem. Lett. 1982, 1169. (e) Mukaiyama, T.; Suzuki, K.; Yamada, T. Chem. Lett. 1982, 929. (f) Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pirrung, M. C.; White, C. T.; Van Derver, D. J. Org. Chem. 1980, 45, 3846.
    • (1984) J. Chem. Res. , pp. 112
    • Fuganti, C.1    Grasselli, P.2    Servi, S.3    Spreafico, F.4    Zirotti, C.5    Casati, P.6
  • 7
    • 0002149447 scopus 로고
    • For examples of the utility of this empirical rationale, see
    • For examples of the utility of this empirical rationale, see: Kishi, Y. Aldrichimica Acta 1980, 13, 23.
    • (1980) Aldrichimica Acta , vol.13 , pp. 23
    • Kishi, Y.1
  • 8
    • 0000326715 scopus 로고
    • For a review on sp2-sp3conformational isomerism, see
    • For a review on sp2-sp3conformational isomerism, see: Karabatsos, G. J.; Fenolio, D. J. Top. Stereochem. 1969, 5, 167.
    • (1969) J. Top. Stereochem. , vol.5 , pp. 167
    • Karabatsos, G.J.1    Fenolio, D.2
  • 9
    • 0001055167 scopus 로고
    • An analogous transition state has been suggested to explain the stereoselection observed in a highly polarized cycloaddition
    • An analogous transition state has been suggested to explain the stereoselection observed in a highly polarized cycloaddition: DeShong, P.; Leginus, J. M. J. Am. Chem. Soc. 1983, 105, 1686.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 1686
    • DeShong, P.1    Leginus, J.M.2
  • 10
    • 0005203619 scopus 로고
    • For a measure of the donor abilities of trialkylstannyl groups, see
    • For a measure of the donor abilities of trialkylstannyl groups, see: Traylor, T. G.; Berwin, H. J.; Jerkunica, J.; Hall, M. L. Pure Appl. Chem. 1972, 30, 599.
    • (1972) Pure Appl. Chem. , vol.30 , pp. 599
    • Traylor, T.G.1    Berwin, H.J.2    Jerkunica, J.3    Hall, M.L.4
  • 13
    • 0001646696 scopus 로고
    • This order is based upon available A values. (a) i-Pr3Sn = 1.10 kcal/mol: Kitching, W. Olszowy, H. A.; Harvey, K. J. Org. Chem. 1982, 47, 1893. (b) Me = 1.70 kcal/mol: Hirsch, J. A. Top. Stereochem. 1967, I, 199. (c) Me3Si ≃ 2.50 kcal/mol
    • 3Si ≃ 2.50 kcal/mol: Kitching, W. Olszowy, H. A.; Drew, G. M.; Adcock, W. J. Org. Chem. 1982, 47, 5153.
    • (1982) J. Org. Chem. , vol.47 , pp. 5153
    • Kitching, W.1    Olszowy, H.A.2    Drew, G.M.3    Adcock, W.4
  • 14
    • 0021135992 scopus 로고
    • Possibly related stereoelectronic effects have been noted in a recent study of spiro-Claisen rearrangements
    • Possibly related stereoelectronic effects have been noted in a recent study of spiro-Claisen rearrangements: Fraser-Reid, B.; Tulshian, D. B.; Tsang, R.; Lowe, D.; Box, V. G. S. Tetrahedron Lett. 1984, 4579.
    • (1984) Tetrahedron Lett. , pp. 4579
    • Fraser-Reid, B.1    Tulshian, D.B.2    Tsang, R.3    Lowe, D.4    Box, V.G.S.5
  • 15
    • 0001034524 scopus 로고    scopus 로고
    • This has been prepared by a route analogous to that previously reported Details will be disclosed at a later date.
    • This has been prepared by a route analogous to that previously reported: McGarvey, G. J.; Hiner, R. N.; Matsubara, Y.; Oh, T. Tetrahedron Lett. 1983, 2733. Details will be disclosed at a later date.
    • Tetrahedron Lett , vol.1983 , Issue.2733
    • McGarvey, G.J.1    Hiner, R.N.2    Matsubara, Y.3    Oh, T.4
  • 16
    • 33749181514 scopus 로고
    • (b) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 4343. (c) Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 4347. (d) Hasan, I.; Kishi, Y. Tetrahedron Lett. 1980, 4229. (e) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109
    • Bognar, R.; Herczegh, P. Carbohydr. Res. 1976, 52, 11. (b) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 4343. (c) Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 4347. (d) Hasan, I.; Kishi, Y. Tetrahedron Lett. 1980, 4229. (e) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109.
    • (1976) Carbohydr. Res. , vol.52 , pp. 11
    • Bognar, R.1    Herczegh, P.2
  • 18
    • 0006698496 scopus 로고
    • (b) Chamberlin, A. R.; Dezube, M.; Dussault, P.; McMills, M. C. J. Am. Chem. Soc. 1983, 105, 5819
    • Midland, M. M.; Hatterman, R. L. J. Org. Chem. 1981, 46, 1227. (b) Chamberlin, A. R.; Dezube, M.; Dussault, P.; McMills, M. C. J. Am. Chem. Soc. 1983, 105, 5819.
    • (1981) J. Org. Chem. , vol.46 , pp. 1227
    • Midland, M.M.1    Hatterman, R.L.2
  • 20
    • 0019419483 scopus 로고
    • (b) Katuki, T.; Lee, A. W. M.; Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Tuddenham, D.; Walker, F. J. J. Org. Chem. 1982, 47, 1373. (c) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 3943. (d) Christ, W. J.; Cha, J. K.; Kishi, Y. Tetrahedron Lett. 1983, 3947. (e) Stork, G.; Kahn, M. Tetrahedron Lett. 1983, 3951. (f) Larson, E. R.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 6715
    • Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1981, 46, 227. (b) Katuki, T.; Lee, A. W. M.; Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Tuddenham, D.; Walker, F. J. J. Org. Chem. 1982, 47, 1373. (c) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 3943. (d) Christ, W. J.; Cha, J. K.; Kishi, Y. Tetrahedron Lett. 1983, 3947. (e) Stork, G.; Kahn, M. Tetrahedron Lett. 1983, 3951. (f) Larson, E. R.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 6715.
    • (1981) J. Org. Chem. , vol.46 , pp. 227
    • Hauser, F.M.1    Rhee, R.P.2


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