A facile solid-phase synthesis of Baylis-Hillman products from polymeric selenium reagents

B Huang, SR Sheng, YX Huang, Q Xin…

Index: Huang, Bin; Sheng, Shou-Ri; Huang, Yi-Xiang; Xin, Qin; Song, Li-Yan; Luo, Nian-Hua Journal of Chemical Research, 2006 , # 10 p. 623 - 625

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Abstract

Treatment of lithio derivatives of polystyrene-supported methyl α-selenopropionate, 2- selenopropiophenone, 1-selenoethyl phenyl sulfone and diethyl 1-selenoethylphosphonate with aldehydes respectively, followed by cleavage from the polymer by oxidation-elimination with 30% hydrogen peroxide efficiently afforded Baylis-Hillman products in good yields and high purities.

~90%

Dramatic rate acceleration of the Baylis-Hillman reaction in...

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