期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 20, 页码 11110-11114出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202014489
关键词
asymmetric synthesis; dihydropyranones; Meldrum' s acid; organocatalysis; vinylogy
资金
- CNRS (UMR 8182)
- University Paris Saclay
- INSA Rouen Normandy
- Centre National de la Recherche Scientifique (CNRS)
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- Region Normandie (CRUNCh network)
- CINES [A0070810977]
- University of Rouen Normandy
- Charm3AtSynOrg Interlabex
Through Bronsted base organocatalysis, ketone-derived alkylidene Meldrum's acids react with dihydro-2,3-furandione in a formal (4+2) cycloaddition reaction, yielding 3,6-dihydropyran-2-ones with up to 98% ee. This reaction can be extended to other activated ketones, making alkylidene Meldrum's acids a novel C4-synthon in the vinylogous series.
Upon Bronsted base organocatalysis, ketone-derived alkylidene Meldrum's acids proved to be competent vinylogous platforms able to undergo a formal (4+2) cycloaddition reaction with dihydro-2,3-furandione, providing an unprecedented route to 3,6-dihydropyran-2-ones as spiro[4.5]decane derivatives with up to 98 % ee thanks to the commercially available Takemoto catalyst. Preliminary investigation showed that this reaction could be extended to other activated ketones, establishing these alkylidene Meldrum's acids as a novel C4-synthon in the vinylogous series.
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