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

共 37 条

[31] SCHEEREN JW, 1986, RECL TRAV CHIM PAY B, V105, P71
[32] SCHEEREN JW, 1993, METHODEN ORGANISCHEN, P1674
[33] ASYMMETRIC DIELS-ALDER REACTIONS CATALYZED BY CHIRAL OXAZABOROLIDINES - EFFECT OF THE POSITION OF AN ELECTRON-DONOR FUNCTIONALITY IN THE ALPHA-SIDE CHAIN SUBSTITUENT ON THE ENANTIOSELECTIVITY
SEERDEN, JPG
SCHEEREN, HW
[J]. TETRAHEDRON LETTERS, 1993, 34 (16) : 2669 - 2672
[34] ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF CHIRAL SULPHINYLETHENES WITH 1-METHYL-3-OXIDOPYRIDINIUM AND SOME NITRONES
TAKAHASHI, T
FUJII, A
SUGITA, J
HAGI, T
KITANO, K
ARAI, Y
KOIZUMI, T
SHIRO, M
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1379 - 1390
[35] CARBON-CARBON BOND FORMING REACTION ASSISTED BY SILICON TRANSFER - THE REACTION BETWEEN NITRONES AND KETENE SILYL ACETALS
TOMODA, S
TAKEUCHI, Y
NOMURA, Y
[J]. CHEMISTRY LETTERS, 1982, (11) : 1787 - 1790
[36] Tufariello J. J., 1984, 1 3 DIPOLAR CYCLOADD, V2, P83
[37] ASYMMETRIC SYNTHESES WITH CHIRAL OXAZABOROLIDINES
WALLBAUM, S
MARTENS, J
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (12) : 1475 - 1504

← 1 2 3 4 →