Gold(I)-Catalyzed Synthesis of Furopyrans: Insight into Hetero-Diels–Alder Reactions

We report herein the synthesis of complex molecules containing furopyran cores through a gold­(I)-catalyzed hetero-Diels–Alder cascade reaction. During this process, the diene and the dienophile are produced concomitantly by the action of a single catalyst from a single starting material. Moreover,...

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Veröffentlicht in:Organic letters 2019-08, Vol.21 (15), p.6084-6088
Hauptverfasser: Pertschi, Romain, Wagner, Patrick, Ghosh, Nayan, Gandon, Vincent, Blond, Gaëlle
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Sprache:eng
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Zusammenfassung:We report herein the synthesis of complex molecules containing furopyran cores through a gold­(I)-catalyzed hetero-Diels–Alder cascade reaction. During this process, the diene and the dienophile are produced concomitantly by the action of a single catalyst from a single starting material. Moreover, six bonds, four heterocycles, and four controlled stereogenic centers are formed in a one-step operation. DFT calculations provide the mechanistic basis of this unprecedented reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02228