Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Reductive Bis-addition of Aromatic Aldehydes to α,β-Unsaturated Esters via the Use of Sm/Cu(I) in Air: A Route to the Construction of Furofuran Lignans

Reductive Bis-addition of Aromatic Aldehydes to α,β-Unsaturated Esters via the Use of Sm/Cu(I) in Air: A Route to the Construction of Furofuran Lignans
Yongjun Liu, Guang Tian, Yan Qi, Feng Du, Jingjing Li, Yonghong Wen
The novel bis-addition of benzaldehydes to acrylates or maleates was achieved by the direct use of samarium metal with the assistance of CuI under mild conditions under dry air, and the useful 2-hydroxylalkyl-γ-butyrolactons and lignan derivatives were thus constructed with high efficiency. The key factors that influence the reaction efficiency were investigated. The use of potassium iodide and molecular sieves as additives can improve the reaction efficiency remarkably.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00278

DOI: 10.1021/acs.joc.7b00278

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