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Alkynyl- and vinylboronates have been used as dipolarophiles in the 1,3-dipolar cycloaddition reactions of nitrones and nitrile N-oxides. However, it has been shown that the reactivity and selectivity pattern of these boron-activated dipolarophiles is significantly influenced by the oxygen atoms attached to the boron. Preliminary DFT calculations performed in our group suggest the lower electrophilic character of the boron atom relative to their dialkyl counterparts affects the potential energy surfaces to a great extent, making these cycloadditions become classical [3+2] processes. For a related DFT study see: (a) J.A. Sáez, M. Arnó, and L.R. Domingo Tetrahedron 59 2003 9167 9171
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We have come across similar findings when studying the Diels-Alder reactions of alkynylboranes, which makes us believe this behavior could be related to a bifurcation in the potential energy surface. (a) M.A. Silva, S.C. Pellegrinet, and J.M. Goodman J. Org. Chem. 67 2002 8203 8209
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43
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26844566777
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note
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We followed Rastelli's nomenclature for the regiochemistry (A and B pathways generate 4- and 5-borylisoxazolidines, respectively).
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44
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note
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This observation suggests the conclusions drawn with prototype compounds may not be completely valid for real systems and highlights the importance of the model chosen for performing computational studies.
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49
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Several conformational switches in transition structures have been described for other cycloaddition reactions. For example, see: J. Liu, S. Niwayama, Y. You, and K.N. Houk J. Org. Chem. 63 1998 1064 1073
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