Derivatives of (S)-{[2-(methoxymethyl)pyrrolidin-1-yl]-methyl}ferrocene -: New planar chiral ligands

被引:3
作者
Sebesta, R [1 ]
Salisová, M [1 ]
机构
[1] Comenius Univ, Fac Nat Sci, Dept Organ Chem, Bratislava 84215, Slovakia
关键词
amino alcohols; ferrocenes; metallocenes; ferrocenyl ligands; planar chirality; asymmetric catalysis; diethylzinc addition;
D O I
10.1135/cccc20021700
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New planar chiral amino-alcohol ferrocene ligands based on (S)-2-(methoxymethyl) pyrrolidine were synthesized and employed in the enantioselective addition of diethylzinc to benzaldehyde with enantioselectivity up to 82%. The effect of planar chirality was evaluated.
引用
收藏
页码:1700 / 1708
页数:9
相关论文
共 22 条
[1]   On the role of planar chirality in asymmetric catalysis:: A study toward appropriate ferrocene ligands for diethylzinc additions [J].
Bolm, C ;
Muñiz-Fernández, K ;
Seger, A ;
Raabe, G ;
Günther, K .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7860-7867
[2]   The synthesis of novel chiral N,O-ferrocenyl ligands and their application in the addition of diethylzinc to aldehydes [J].
Deng, WP ;
Hou, XL ;
Dai, LX .
TETRAHEDRON-ASYMMETRY, 1999, 10 (24) :4689-4693
[3]  
Enders D, 2000, EUR J ORG CHEM, V2000, P3399
[4]   ASYMMETRIC-SYNTHESIS CATALYZED BY TRANSITION-METAL COMPLEXES WITH FUNCTIONALIZED CHIRAL FERROCENYLPHOSPHINE LIGANDS [J].
HAYASHI, T ;
KUMADA, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (12) :395-401
[5]   CATALYTIC ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES [J].
KITAMURA, M ;
SUGA, S ;
KAWAI, K ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6071-6072
[6]   ortho-silylation of 2,2′-bis(oxazolinyl)-1,1′-bis(diphenylphosphino)ferrocenes and remarkable effect of the silyl groups on the enantio selectivity in Pd-catalyzed asymmetric allylic alkylation [J].
Lee, S ;
Koh, JH ;
Park, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 637 :99-106
[7]   STEREOSELECTIVE SYNTHESES .5. CORRELATION OF CENTRAL AND PLANAR CHIRALITY IN FERROCENE DERIVATIVES [J].
MARQUARDING, D ;
KLUSACEK, H ;
GOKEL, G ;
HOFFMANN, P ;
UGI, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5389-+
[8]  
Muñiz K, 2000, CHEM-EUR J, V6, P2309, DOI 10.1002/1521-3765(20000703)6:13<2309::AID-CHEM2309>3.0.CO
[9]  
2-N
[10]  
NISHIBAYASHI Y, 1995, SYNLETT, P79