Tetrahedron letters

One-pot facile conversion of Baylis–Hillman adduct into N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2, 6-dione. Formal synthesis of tacamonine

CY Chen, MY Chang, RT Hsu, ST Chen, NC Chang

文献索引：Chen, Chung-Yi; Chang, Meng-Yang; Hsu, Ru-Ting; Chen, Shui-Tein; Chang, Nein-Chen Tetrahedron Letters, 2003 , vol. 44, # 47 p. 8627 - 8630

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被引用次数: 16

摘要

A stepwise [3+ 3] strategy to N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2, 6- dione 1 used various N-alkyl α-substituted sulfonylacetamides 2 and α, β-unsaturated esters 3 as starting materials. α, β-Unsaturated esters 3 were generated by Baylis–Hillman reaction. A ring closure mechanism was proposed for the reactions. This method provides a convenient formal synthesis of tacamonine.