A chiral auxiliary derived from levoglucosenone in asymmetric Diels-Alder transformations |
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| Authors: | Ariel M. Sarotti |
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| Affiliation: | Instituto de Química Orgánica de Síntesis, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario—CONICET Suipacha 531, S2002LRK Rosario, Argentina |
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| Abstract: | The Diels-Alder reaction of the acrylate derived from levoglucosenone with cyclopentadiene was studied under several conditions, in the presence and absence of a Lewis acid. The results showed satisfactory diastereomeric excess and the ratio of cycloadducts was found to depend on the reaction conditions. A reversal in stereoselectivity was observed when EtAlCl2 or Et2AlCl were employed as Lewis acids. |
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| Keywords: | Levoglucosenone Chiral auxiliary Diels-Alder Cycloadditions Acrylate |
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