Reversal of facial selectivity in complex Diels-Alder reactions |
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Authors: | Funel Jacques-Alexis Ricard Louis Prunet Joëlle |
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Affiliation: | Laboratoire de Synthèse Organique, UMR CNRS 7652, Ecole Polytechnique, DCSO, Palaiseau, France. |
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Abstract: | A complex Diels-Alder reaction between a semi-cyclic diene with allylic silyloxy substituents and a bromo enone presented an unusual diastereoselectivity: attack of the diene occured on its more hindered face, and this reversal of selectivity was shown to be induced by the presence of a bromo substituent in the dienophile. |
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