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
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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页码:4419 / 4422
页数:4
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