A novel design of a levoglucosenone derived chiral auxiliary |
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| Authors: | Ariel M Sarotti |
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| Institution: | 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: | A two-step general approach to a new chiral auxiliary starting from levoglucosenone is reported. The compound is obtained by a 4+2] cycloaddition reaction with anthracene followed by a diastereoselective reduction of the C-2 keto function in high overall yield. The auxiliary has been used as chiral template in an asymmetric Diels-Alder reaction of the corresponding acrylic ester derivative with cyclopentadiene and shown to be efficient for asymmetric induction. |
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| Keywords: | Levoglucosenone Chiral auxiliary Diels-Alder Cycloaddition |
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