Issue 29, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
20 Jan 2017
Accepted
26 Jun 2017
First published
28 Jun 2017

Org. Biomol. Chem., 2017,15, 6098-6103

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, 15, 6098 DOI: 10.1039/C7OB00165G

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