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ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF NITRONES WITH KETENE ACETALS CATALYZED BY CHIRAL OXAZABOROLIDINES

被引：101
|
作者：
SEERDEN, JPG [1 ]
REIMER, AWASO [1 ]
SCHEEREN, HW [1 ]
机构：
[1] UNIV NIJMEGEN,NSR CTR MOLEC STRUCT DESIGN & SYNTH,DEPT ORGAN CHEM,6525 ED NIJMEGEN,NETHERLANDS
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 25期
关键词：
D O I：
10.1016/S0040-4039(00)73373-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymetric 1,3-dipolar cycloaddition of nitrones with ketene acetals is strongly catalyzed by chiral oxazaborolidines derived from N-tosyl-L-alpha-amino acids. The 5,5-dialkoxyisoxazolidines are obtained regioselectively in high yield with high stereoselectivity and moderate enantioselectivity Icp to 62% ee. Mild hydrogenolysis of the N-O bond yields quantitatively the corresponding beta-amino-ester.
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收藏
页码：4419 / 4422
页数：4
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