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Asymmetric synthesis of new γ-butenolides via organocatalyzed epoxidation of chalcones

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Abstract

γ-Butenolides have been recognized as an important structural framework in a number of natural products and medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted γ-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product, furnishing new enantiomerically enriched γ-butenolides in moderate overall yield and good enantiomeric excess.

Graphical abstract: Asymmetric synthesis of new γ-butenolides via organocatalyzed epoxidation of chalcones

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Publication details

The article was received on 20 Jan 2017, accepted on 26 Jun 2017 and first published on 28 Jun 2017


Article type: Communication
DOI: 10.1039/C7OB00165G
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Asymmetric synthesis of new γ-butenolides via organocatalyzed epoxidation of chalcones

    L. C. C. Vieira, B. T. Matsuo, L. S. R. Martelli, M. Gall, M. W. Paixão and A. G. Corrêa, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00165G

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