Organocatalytic β,γ-Selective Activation of Deconjugated Butenolides Access to Chiral Tricyclic Chroman-butyrolactones

A highly efficient method for the β,γ-selective activation of deconjugated butenolides has been developed through an organocatalytic asymmetric vinylogous cascade reaction. This protocol enables the construction of a broad range of substituted tricyclic chroman-butyrolactones by vinylogous Michael/o...

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Veröffentlicht in:Journal of organic chemistry 2021-09, Vol.86 (18), p.12821-12830
Hauptverfasser: Zheng, Yangqing, Jiang, Weichao, Tan, Jingbo, Yan, Juzhang, Zhan, Ruoting, Huang, Huicai
Format: Artikel
Sprache:eng
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Zusammenfassung:A highly efficient method for the β,γ-selective activation of deconjugated butenolides has been developed through an organocatalytic asymmetric vinylogous cascade reaction. This protocol enables the construction of a broad range of substituted tricyclic chroman-butyrolactones by vinylogous Michael/oxa-Michael pathways in good yield (up to 89%) with good to high enantioselectivity (up to 97:3 er) and excellent diastereoselectivity. The ring-opening esterification of butyrolactones was also demonstrated.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01449