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Synlett 1999; 1999(11): 1681-1703
DOI: 10.1055/s-1999-2920
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On the Origins of Diastereofacial Selectivity in Diels-Alder Cycloadditions

James M. Coxon* , Robert D. J. Froese, Bishwajit Ganguly, Alan P. Marchand, Keiji Morokuma
  • *Department of Chemistry, University of Canterbury, Christchurch, New Zealand; Fax +64 (3) 3 64 21 10; E-mail: J.Coxon@its.canterbury.ac.nz
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Publication Date:
31 December 1999 (online)

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We review current understanding of p-facial selectivity in Diels-Alder reactions. High level calculations that include electron correlation are necessary to predict facial selectivity. Within the next decade theoretical calculations of transition states should become sufficiently fast to enable organic chemists to predict p-facial selectivity even in moderately complex systems.

facial selectivity - acetylene Diels-Alder - ethylene Diels-Alder - ab initio - semi empirical - correlation diagram - cage compounds

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