Solid-phase synthesis:: Intramolecular azomethine ylide cycloaddition (→proline) and carbanilide cyclization (→hydantoin) reactions

被引：69

作者：

Gong, YD

Najdi, S

Olmstead, MM

Kurth, MJ ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

[2] Al Quds Univ, Dept Chem, E Jerusalem, Israel

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 09期

关键词：

D O I：

10.1021/jo9800210

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, diastereoselective route to 2,5,6,7-tetrasubstituted-1H-pyrrolo[1,2-c]imidazoles has been developed using solid-phase intramolecular azomethine ylide cycloaddition and carbanilide cyclization chemistries. To successfully execute this eight-step protocol in the solid phase, it was necessary to insert a spacer moiety between the resin and glycinate functional group. Experiments addressing the stereoselectivity of the 1,3-dipolar cycloaddition step as well as the cyclative release step are also presented.

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页码：3081 / 3086

页数：6

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