1,3-Dipolar Cycloaddition of Nitrones with 5-Methylenehydantoins: Synthesis and Transformation of New Spirohydantoin Derivatives

被引：11
|
作者：
Bahy, Amira [1 ]
Kacem, Yakdhane [1 ]
Ben Hassine, Bechir [1 ]
机构：
[1] Fac Sci, Lab Asymmetr Organ Synth & Homogeneous Catalysis, Monastir 5019, Tunisia
来源：
SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 09期
关键词：
1; 3-Dipolar cycloaddition; 5-methylenehydantoins; nitrones; regioselectivity; stereoselectivity; METHYLENE-GAMMA-BUTYROLACTONES; ENANTIOSELECTIVE SYNTHESIS; SOLUTION-PHASE; ALPHA; HYDANTOCIDIN; ANALOGS; STEREOSELECTIVITY; (+)-HYDANTOCIDIN; GLUCOFURANOSE; METABOLITE;
D O I：
10.1080/00397910903097237
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,3-Dipolar cycloaddition of various acyclic nitrones with 5-methylenehydantoin derivatives afforded new chiral spiroadducts in good yields. All the spirohydantoins were obtained through a regio- and stereospecific pathway, and the spirocarbon atom was linked to the isoxazolidine oxygen atom. A representative example of the reduction of the spirohydantoin 8 with Zn/AcOH led to the substituted 1,3-aminoalcohol hydantoin 20.
引用
收藏
页码：1377 / 1390
页数：14
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