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

页码：1377 / 1390

页数：14