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

Autores:

Vieira, Lucas C. C.1 2 ; Matsuo, Bianca T.1 ; Martelli, Lorena S. R.1 ; Gall, Mayara1 ; Paixao, Marcio W.1 ; Correa, Arlene G.1


Resumo:

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.


 Centre of Excellence for Research in Sustainable Chemistry, Department of Chemistry, Federal University of São Carlos, São Carlos, Brazil

 Instituto de Engenharia, Universidade Federal de Mato Grosso, 78060-900, Cuiabá, Brazil


Link to full article:

http://pubs.rsc.org/en/Content/ArticleLanding/2017/OB/C7OB00165G#!divAbstract