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.

引用

页码：4419 / 4422

页数：4

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