Diastereofacial selectivities of substituted 5-aza- and 5-bora-2- adamantanones. Application of the complexation model and its ab initio MO investigation

Tetrahedron

Volumn 55, Issue 49, 1999, Pages 14211-14218

  Yadav, Veejendra K ^a   Senthil, Govindraji ^a   Jeyaraj, Duraiswamy A ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Adamantanones; Cation complexation; Diastereoselection; Stereoelectronic effects

Indexed keywords

CYCLOHEXANONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; COMPLEX FORMATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033520932     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00888-1     Document Type: Article

References (33)

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21. 7 The cation complexed to the carbonyl is expected to lie in the nodal plane of the carbonyl π bond as established by X-ray structure of a methylaluminum diaryloxide complex of benzophenone. Power, M. B.; Bott, S. G.; Atwood, J. L.; Barron, A. R. J. Am. Chem. Soc. 1990, 112, 3446.
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26. 10 All the calculations were performed using the program Gaussian 94, Revision C.2. See, Frish, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
27. -, see Pelter, A.; Hutchings, M. G.; Smith, K. J. Chem. Soc. Chem. Commun. 1973, 186; For the addition of 1-lithio-1,1-bis(phenylthio)alkane, see Hughes, R. J.; Neube, S.; Pelter, A.; Smith, K.; Negishi, Ei-chi; Yoshida, T. J. Chem. Soc. Perkin Trans. I 1977, 1172.
28. -, see Pelter, A.; Hutchings, M. G.; Smith, K. J. Chem. Soc. Chem. Commun. 1973, 186; For the addition of 1-lithio-1,1-bis(phenylthio)alkane, see Hughes, R. J.; Neube, S.; Pelter, A.; Smith, K.; Negishi, Ei-chi; Yoshida, T. J. Chem. Soc. Perkin Trans. I 1977, 1172.
29. -, see Pelter, A.; Hutchings, M. G.; Smith, K. J. Chem. Soc. Chem. Commun. 1973, 186; For the addition of 1-lithio-1,1-bis(phenylthio)alkane, see Hughes, R. J.; Neube, S.; Pelter, A.; Smith, K.; Negishi, Ei-chi; Yoshida, T. J. Chem. Soc. Perkin Trans. I 1977, 1172.
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33. 13 For a recent account of the diastereoselectivities of various systems including the 5-hetero-2-adamantanones, see, Mehta, G.; Chandrasekhar. J. Chem. Rev. 1999, 99, 1437.