METAL-ION CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES OF ALPHA-AMINO ESTERS

被引：60

作者：

BARR, DA

DORRITY, MJ

GRIGG, R

MALONE, JF

MONTGOMERY, J

RAJVIROONGIT, S

STEVENSON, P

机构：

[1] UNIV LEEDS,SCH CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND

[2] MAHIDOL UNIV,DEPT CHEM,BANGKOK 10700,THAILAND

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)97119-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloaddition of a range of imines of α-amino esters to homochiral menthyl acrylate proceeds with complete asymmetric induction at room temperature in the presence of silver(I), lithium(I) and thallium(I) salts. The imine of 2-aminomethylpyridine reacts similarly. Reversal of cycloaddition regiochemistry, together with complete asymmetric induction, occurs when titanium (IV) complexes are used as catalysts. The absolute configuration of one of the cycloadducts has been established by X-ray crystallography. © 1990.

引用

页码：6569 / 6572

页数：4

共 5 条

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[2] TANDEM MICHAEL ADDITION-1,3-DIPOLAR CYCLO-ADDITION OF IMINES OF ALPHA-AMINO-ACID ESTERS AND AMINOACETONITRILE
BARR, DA
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[3] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .15. AMINE GENERATED AZAALLYL ANIONS VERSUS METALLO-1,3-DIPOLES IN CYCLO-ADDITIONS OF ALPHA-AMINO-ACID ESTERS - FACILE REGIO-SPECIFIC AND STEREO-SPECIFIC FORMATION OF PYRROLIDINES
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KEMP, J
MCMEEKIN, P
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[J]. TETRAHEDRON, 1988, 44 (02) : 557 - 570
[4] TI(IV) MEDIATED TRANS-ESTERIFICATION AND REGIO-SPECIFIC AND STEREO-SPECIFIC CYCLO-ADDITION OF IMINES OF ALPHA-AMINO ESTERS - REVERSAL OF NORMAL REGIOCHEMISTRY
BARR, DA
GRIGG, R
SRIDHARAN, V
[J]. TETRAHEDRON LETTERS, 1989, 30 (35) : 4727 - 4730
[5] KANEMASA S, 1990, TETRAHEDRON LETT, V31, P3633

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