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Volumn 99, Issue 5, 1999, Pages 1225-1241

Using Perturbation and Frontier Molecular Orbital Theory to Predict Diastereofacial Selectivity

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EID: 0000150775     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr980382f     Document Type: Article
Times cited : (58)

References (84)
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    • Franck, R.W.1
  • 3
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    • note
    • In any case, each calculation must be carefully considered individually. One should note that restricted Hartree-Fock (RHF) calculations on transition states where the nucleophile is a small anion (e.g., hydride) are suspect because the probable single electron transfer from the anion to the ketone cannot be treated by this method. See section III.B.1 for more detailed discussion.
  • 22
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    • (1962) Chemia , vol.16 , pp. 173
  • 25
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    • note
    • Figure 2 is drawn with the orbital splittings approximately of equal magnitude for the symmetrical and unsymmetrical orbital interactions. This is strictly true only for the approximation where S (overlap) = 0.
  • 34
    • 0346047580 scopus 로고    scopus 로고
    • note
    • One should note that the ΔHreaction of the reduction product depends on the nucleophile. Thus, the selectivity for attack by methide (for example) should differ from that of hydride.
  • 36
    • 0012474277 scopus 로고
    • Oxford University Press: London
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    • (1952) Hyperconjugation
    • Baker, J.W.1
  • 58
    • 33845556545 scopus 로고
    • An earlier paper by Paddon-Row and Houk et al. reported calculations (HF/STO-3G) on propene with a fixed hydride, proton, or H-atom 2 Å above the olefinic plane, in what may be the earliest report of this type. (J. Am. Chem. Soc. 1981, 103, 2438-40). We used this methodology for formaldehyde plus a hydride. This yielded charge transfers of 0.81, 0.54, and 0.22 at 1.4, 2.0, and 8.0 Å, respectively, above the C=O.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 2438-2440
    • Paddon-Row1    Houk2
  • 61
    • 0346678199 scopus 로고    scopus 로고
    • note
    • Some of the compounds have oxygens as part of both substituents at the 4-position.
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    • 0039429266 scopus 로고
    • Schubert, W. M.; Sweeney, W. A. J. Org. Chem. 1956, 21, 119.; Schubert, W. M.; Robins, J.; Haun, J. L. J. Am. Chem. Soc. 1957, 79, 910. Schubert, W. M.; Craven, J.; Minton, R. G.; Murphy, R. B. Tetrahedron 1959, 5, 194. Schubert, W. M.; Minton, R. G. J. Am. Chem. Soc. 1960, 82, 6188.
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    • Schubert, W. M.; Sweeney, W. A. J. Org. Chem. 1956, 21, 119.; Schubert, W. M.; Robins, J.; Haun, J. L. J. Am. Chem. Soc. 1957, 79, 910. Schubert, W. M.; Craven, J.; Minton, R. G.; Murphy, R. B. Tetrahedron 1959, 5, 194. Schubert, W. M.; Minton, R. G. J. Am. Chem. Soc. 1960, 82, 6188.
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    • Schubert, W. M.; Sweeney, W. A. J. Org. Chem. 1956, 21, 119.; Schubert, W. M.; Robins, J.; Haun, J. L. J. Am. Chem. Soc. 1957, 79, 910. Schubert, W. M.; Craven, J.; Minton, R. G.; Murphy, R. B. Tetrahedron 1959, 5, 194. Schubert, W. M.; Minton, R. G. J. Am. Chem. Soc. 1960, 82, 6188.
    • (1959) Tetrahedron , vol.5 , pp. 194
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  • 67
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    • Schubert, W. M.; Sweeney, W. A. J. Org. Chem. 1956, 21, 119.; Schubert, W. M.; Robins, J.; Haun, J. L. J. Am. Chem. Soc. 1957, 79, 910. Schubert, W. M.; Craven, J.; Minton, R. G.; Murphy, R. B. Tetrahedron 1959, 5, 194. Schubert, W. M.; Minton, R. G. J. Am. Chem. Soc. 1960, 82, 6188.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 6188
    • Schubert, W.M.1    Minton, R.G.2


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