Glycerol/hypophosphorous acid and PhSeSePh: an efficient and selective system for reactions in the carbon-carbon double bond of (E)-chalcones

Journal of the Brazilian Chemical Society

Katiúcia D. Mesquita¹  Bianca Waskow¹  Ricardo F. Schumacher¹  Gelson Perin¹  Raquel G. Jacob¹  Diego Alves¹ 

[1] ,Universidade Federal de Pelotas Centro de Ciências Químicas, Farmacêuticas e de Alimentos Laboratório de Síntese Orgânica LimpaPelotas RS ,Brazil

关键词: chalcones;    selenium;    glycerol;    reduction;    zingerone;   

DOI  :  10.5935/0103-5053.20140104

来源: SciELO

【 摘 要 】

We describe herein our results for the reaction of benzeneselenol, generated in situ by reaction of diphenyl diselenide with H3PO2, with various (E)-chalcones using glycerol as solvent. Using our optimized reaction conditions, a range of chemoselective 1,4-reduction products could be obtained in good yields. The glycerol/H3PO2 system can be easily recovered and reused in chemoselective 1,4-reductions for successive cycles without loss of efficiency. Additionally, under 1,4-reducing reaction conditions, the natural product zingerone can be synthesized in good yield.

【 授权许可】

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