Design and synthesis of a chiral N-tethered bis(imidazoline) ligand

被引：27

作者：

Arai, T ^{[1
]}

Mizukami, T

Yokoyama, N

Nakazato, D

Yanagisawa, A

机构：

[1] Chiba Univ, Fac Sci, Dept Chem, Inage 2638522, Japan

[2] Chiba Univ, Grad Sch Sci & Technol, Inage 2638522, Japan

来源：

SYNLETT | 2005年 / 17期

关键词：

asymmetric catalysis; ligands; imidazoline; copper; cyclopropanation;

D O I：

10.1055/s-2005-917101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral nitrogen-tethered bis (imidazoline) ligand (Nb-imidazoline) was newly designed and synthesized in a divergent strategy. Thus, a single coupling reaction of primary amine with two molecules of chloromethylated imidazoline provided the Nb-imidazoline. The copper(II) triflate complex of Nb-imidazoline catalyzed a trans-selective cyclopropanation of styrene with ethyl diazoacetate to give the adduct in high chemical yield with good enantiomeric excess up to 83%.

引用

页码：2670 / 2672

页数：3

共 18 条

[1] Insights into CO/styrene copolymerization by using PdII catalysts containing modular pyridine-imidazoline ligands
Bastero, A
Claver, C
Ruiz, A
Castillón, S
Daura, E
Bo, C
Zangrando, E
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (15) : 3747 - 3760
[2] Beller M., 2004, TRANSITION METALS OR, DOI 10.1002/9783527619405
[3] Svnthesis of a new chiral N,N,N-tridentate pyridinebisimidazoline ligand library and its application in Ru-catalyzed asymmetric epoxidation
Bhor, S
Anilkumar, G
Tse, MK
Klawonn, M
Dobler, C
Bitterlich, B
Grotevendt, A
Beller, M
[J]. ORGANIC LETTERS, 2005, 7 (16) : 3393 - 3396
[4] Probing electronic effects in the asymmetric Heck reaction with the BIPI ligands
Busacca, CA
Grossbach, D
So, RC
O'Brien, EM
Spinelli, EM
[J]. ORGANIC LETTERS, 2003, 5 (04) : 595 - 598
[5] Casey M, 2003, SYNLETT, P102
[6] Chiral pyridylimidazolines: synthesis, arene ruthenium complexes and application in asymmetric catalysis
Davenport, AJ
Davies, DL
Fawcett, J
Russell, DR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (13): : 1500 - 1503
[7] C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis
Ghosh, AK
Packiarajan, M
Cappiello, J
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (01) : 1 - 45
[8] Cu(II)-aza(bisoxazoline)-catalyzed asymmetric benzoylations
Gissibl, A
Finn, MG
Reiser, O
[J]. ORGANIC LETTERS, 2005, 7 (12) : 2325 - 2328
[9] An efficient method for the synthesis of enantiopure phosphine-imidazoline ligands:: application to the Ir-catalyzed hydrogenation of imines
Guiu, E
Claver, C
Benet-Buchholz, J
Castillón, S
[J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (21) : 3365 - 3373
[10] MULTIMACROCYCLIC COMPOUNDS .4. INTERNAL TRIMERISATION OF TRIPLE BONDS OF LINEAR TRIYNES ON A ZIEGLER CATALYST
HUBERT, AJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (20): : 1984 - &

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