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 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.1c01449 |