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

被引：13

作者：

Chen, CY

Chang, MY ^{[1
]}

Hsu, RT

Chen, ST

Chang, NC

机构：

[1] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

[2] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan

[3] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 47期

关键词：

stepwise [3+3] strategy; Baylis-Hillman reaction; glutarimide; tacamonine;

D O I：

10.1016/j.tetlet.2003.08.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stepwise [3+3] strategy to N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione 1 used various N-alkyl a-substituted sulfonylacetamides 2 and alpha,beta-unsaturated esters 3 as starting materials. alpha,beta-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. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8627 / 8630

页数：4

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[1] The use of enantiomerically pure N-sulfinimines in asymmetric Baylis-Hillman reactions [J].