Cleft molecules as organocatalysts in an asymmetric hetero-Diels–Alder reaction |
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| Affiliation: | 1. Division of Organic Chemistry, Kemicentrum, Lund University, PO Box 124, SE-221 00 Lund, Sweden;2. Acadia Pharmaceuticals AB, Medeon Science Park, SE-205 12 Malmö, Sweden |
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| Abstract: | The synthesis and application of chiral carbocyclic cleft molecules derived from 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione in the hetero-Diels–Alder reaction of benzaldehydes and aminodiene 14 is presented. Catalysis by single hydrogen-bond activation gave up to 52% ee. |
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