Synthesis of ferrocene substituted pyrrolidine derivatives via Et2Zn catalyzed 1,3-dipolar cycloaddition reactions of azomethine ylides

被引:10
作者
Dogan, Ö [1 ]
Koyuncu, H [1 ]
机构
[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
关键词
ferrocene; pyrrolidine; diethylzinc catalysis; 1,3-dipolar cycloadditions;
D O I
10.1016/S0022-328X(01)01034-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Synthesis of ferrocene substituted pyrrolidine derivatives via diethylzinc catalyzed 1,3-dipolar cycloadditions of azomethine ylides is described. Azomethine ylides were generated from glycine methyl ester and ferrocenecarboxaldehyde by the 'imine tautomerization' method and trapped with dipolarophiles to give the corresponding cycloadducts in reasonable yields and high regio- and stereoselectivity. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:135 / 138
页数:4
相关论文
共 27 条
[1]   Study on ferrocenes, part 6.: 1,3-dipolar cycloadditions of heterocyclic hydrazones of formylferrocene [J].
Abrán, A ;
Csámpai, A ;
Böcskei, Z ;
Sohár, P .
TETRAHEDRON, 1999, 55 (17) :5441-5448
[2]   CHIRAL CO(II) AND MN(II) CATALYSTS FOR THE 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES DERIVED FROM ARYLIDENE IMINES OF GLYCINE [J].
ALLWAY, P ;
GRIGG, R .
TETRAHEDRON LETTERS, 1991, 32 (41) :5817-5820
[3]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .8. PYRROLIDINES AND DELTA-5-PYRROLINES (3,7-DIAZABICYCLO[3.3.0]OCTENES) FROM THE REACTION OF IMINES OF ALPHA-AMINO-ACIDS AND THEIR ESTERS WITH CYCLIC DIPOLAROPHILES - MECHANISM OF RACEMIZATION OF ALPHA-AMINO-ACIDS AND THEIR ESTERS IN THE PRESENCE OF ALDEHYDESN [J].
AMORNRAKSA, K ;
GRIGG, R ;
GUNARATNE, HQN ;
KEMP, J ;
SRIDHARAN, V .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (10) :2285-2296
[4]  
[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3
[5]   X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .43. METAL-ION CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES AND MENTHYL ACRYLATE [J].
BARR, DA ;
DORRITY, MJ ;
GRIGG, R ;
HARGREAVES, S ;
MALONE, JF ;
MONTGOMERY, J ;
REDPATH, J ;
STEVENSON, P ;
THORNTONPETT, M .
TETRAHEDRON, 1995, 51 (01) :273-294
[6]   STUDY OF THE REGIOCHEMISTRY AND STEREOCHEMISTRY OF THE [3 + 2] CYCLO-ADDITION BETWEEN NONSTABILIZED AZOMETHINE YLIDES GENERATED FROM TERTIARY AMINE N-OXIDES AND VARIOUS DIPOLAROPHILES [J].
CHASTANET, J ;
ROUSSI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3808-3812
[7]  
DOGAN O, 2001, TURK J CHEM, V25
[8]   Synthesis of chiral primary 1-ferrocenylalkylamines via highly diastereoselective addition of organolithium compounds to ferrocenecarboxaldehyde imine derived from (S)-2-methoxy-1-phenylethylamine [J].
Fukuda, T ;
Takehara, A ;
Haniu, N ;
Iwao, M .
TETRAHEDRON-ASYMMETRY, 2000, 11 (20) :4083-4091
[9]   Stereocontrolled 1,3-dipolar cycloadditions using Oppolzer's camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides [J].
Garner, P ;
Dogan, Ö ;
Youngs, WJ ;
Kennedy, VO ;
Protasiewicz, J ;
Zaniewski, R .
TETRAHEDRON, 2001, 57 (01) :71-85
[10]   Friedel-Crafts alkylation of ferrocene with Z-cyclooctene and cyclohexene [J].
Grevels, FW ;
Kuran, A ;
Özkar, S ;
Zora, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 587 (01) :122-126