The butenolide skeleton is one of the more common to natural products and bioative compounds, thus its synthesis has afforded much attention from synthetic chemists in recent years. Here, Xiamong Feng and colleagues from the Key Laboratory of Green Chemistry and Technology at Sichuan University have devised a simple route that affords the desired γ-butenolide compounds in high yields with high levels of selectivity.
By using a chiral N,N‘-dioxide-scandium catalyst in an asymmetric vinylogous Mukaiyama–Michael reaction they were able to form highly functionalized chiral γ-substituted butenolides with broad substrate scope, with up to 92% ee. The pathway is air stable and produces product on a gram scale.
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Highly enantioselective synthesis of γ-substituted butenolides via the vinylogous Mukaiyama–Michael reaction catalyzed by a chiral scandium(III)–N,N′-dioxide complex
Qi Zhang, Xiao Xiao, Lili Lin, Xiaohua Liu and Xiaoming Feng
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05558E
