TRANSITION-METAL-CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS BETWEEN ALKENES AND NITRONES

被引：156

作者：

GOTHELF, KV ^{[1
]}

JORGENSEN, KA ^{[1
]}

机构：

[1] UNIV AARHUS,DEPT CHEM,DK-8000 AARHUS C,DENMARK

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 19期

关键词：

D O I：

10.1021/jo00098a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition-metal-catalyze denantioselective 1,3-dipolar cycloaddition reaction between alkenes and nitrones has been developed employing 10 mol % of a chiral titanium catalyst generated in situ from Ti(i-OPr)(2)Cl-2 and chiral diols. Diastereofacial discrimination in favor of the exo isomer was achieved in up to a 95:5 ratio. Isoxazolidines with an optical purity of up to 62% ee are obtained from this reaction. By precipitation of a racemate of one of the isoxazolidines an optical purity of >95% ee is obtained.

引用

页码：5687 / 5691

页数：5

共 46 条

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