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
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.
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页码:5687 / 5691
页数:5
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