Structurally diverse second-generation [2.2]paracyclophane ketimines with planar and central chirality:: Syntheses, structural determination, and evaluation for asymmetric catalysis

被引：29

作者：

Lauterwasser, F

Nieger, M

Mansikkamäki, H

Nättinen, K

Bräse, S

机构：

[1] Univ Karlsruhe, Inst Organ Chem, TH, D-76131 Karlsruhe, Germany

[2] Univ Bonn, Inst Anorgan Chem, D-53121 Bonn, Germany

[3] Univ Jyvaskyla, Dept Chem, SF-40351 Jyvaskyla, Finland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2005年 / 11卷 / 15期

关键词：

asymmetric catalysis; chirality; cyclophanes; ketimines; zinc;

D O I：

10.1002/chem.200500146

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A set of 20 novel [2.2]paracyclophane ketimines with planar and central chirality has been synthesized from enantiomerically pure and racemic 5-acyl-4- hydroxy[2.2]paracyclophane and a-branched chiral amines. Their X-ray structures were determined to elucidate the three-dimensional structures and the absolute configuration. The ketimines were used as catalysts in the asymmetric 1,2-addition reactions of diethylzinc with substituted benzaldehydes to furnish chiral alcohols in up to 95% ee.

引用

收藏

页码：4509 / 4525

页数：17

相关论文

共 75 条

[1] SYNTHESIS, RESOLUTION AND ABSOLUTE-CONFIGURATION DETERMINATION OF (S)-4-FORMYL-5-HYDROXY[2.2]PARACYCLOPHANE AND (R)-4-FORMYL-5-HYDROXY[2.2]PARACYCLOPHANE AND ITS APPLICATION IN THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

ANTONOV, DY ;

BELOKON, YN ;

IKONNIKOV, NS ;

ORLOVA, SA ;

PISAREVSKY, AP ;

RAEVSKI, NI ;

ROZENBERG, VI ;

SERGEEVA, EV ;

STRUCHKOV, YT ;

TARAROV, VI ;

VORONTSOV, EV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (14) :1873-1879

[2] Asymmetric trimethylsilylcyanation of benzaldehyde catalyzed by (salen)Ti(IV) complexes derived from (R)- and/or (S)-4-hydroxy-5-formyl[2.2]paracyclophane and diamines [J].

Belokon, Y ;

Moscalenko, M ;

Ikonnikov, N ;

Yashkina, L ;

Antonov, D ;

Vorontsov, E ;

Rozenberg, V .

TETRAHEDRON-ASYMMETRY, 1997, 8 (19) :3245-3250

[3]

Blaser H. U., 2003, ASYMMETRIC CATALYSIS

[4] Synthesis of iridium complexes with novel planar chiral chelating imidazolylidene ligands [J].

Bolm, C ;

Focken, T ;

Raabe, G .

TETRAHEDRON-ASYMMETRY, 2003, 14 (12) :1733-1746

[5]

Bolm C, 2000, SYNLETT, P899

[6] Planar-chiral ferrocenes in asymmetric catalysis:: The impact of stereochemically inhomogeneous ligands [J].

Bolm, C ;

Muñiz, K ;

Hildebrand, JP .

ORGANIC LETTERS, 1999, 1 (03) :491-493

[7] 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

[8] Planar chiral PHANOLs as double hydrogen bonding donor organocatalysts: Synthesis and catalysis [J].

Braddock, DC ;

MacGilp, ID ;

Perry, BG .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1117-1130

[9] Planar and central chiral [2.2]paracyclophanes as powerful catalysts for asymmetric 1,2-addition reactions [J].

Bräse, S ;

Dahmen, S ;

Höfener, S ;

Lauterwasser, F ;

Kreis, M ;

Ziegert, RE .

SYNLETT, 2004, (15) :2647-2669

[10] Recent advances in asymmetric C-C and C-heteroatom bond forming reactions using polymer-bound catalysts [J].

Bräse, S ;

Lauterwasser, F ;

Ziegert, RE .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (08) :869-929

← 1 2 3 4 5 6 7 8 →