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.

¹  Centre of Excellence for Research in Sustainable Chemistry, Department of Chemistry, Federal University of São Carlos, São Carlos, Brazil

²  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