Second-generation N,O-[2.2]paracyclophane ketimine ligands for the alkenylzinc addition to aliphatic and aromatic aldehydes:: Scope and limitations

被引：38

作者：

Lauterwasser, Frank ^{[1
]}

Gall, Julia ^{[1
]}

Hoefener, Sebastian ^{[1
]}

Braese, Stefan ^{[1
]}

机构：

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 15期

关键词：

alkenylzinc reagents; asymmetric catalysis; chiral allylic alcohols; N; O ligands; paracyclophanes;

D O I：

10.1002/adsc.200606193

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Second generation N,O-[2.2]paracy-clophane ketimine ligands were investigated for their ability to catalyze the 1,2-addition of alkenylzinc reagents to aliphatic and aromatic aldehydes with special focus on functionalized substrates. For aliphatic aldehydes, which have always been challenging in this field, remarkably high enantiomeric excesses could be determined (50-95 % ee). However, alkenylzinc reagents bearing heteroatoms proved to be demanding substrates for this system.

引用

页码：2068 / 2074

页数：7

共 70 条

[1]

Banwell MG, 2004, HETEROCYCLES, V62, P713

[2] 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

[3]

Bolm C, 2000, SYNLETT, P899

[4] VINYLATION ELECTROPHILIC CYCLIZATION OF ALDOPENTOSES - EASY AND STEREOSELECTIVE ACCESS TO C-GLYCOPYRANOSIDES OF RARE SUGARS [J].

BOSCHETTI, A ;

NICOTRA, F ;

PANZA, L ;

RUSSO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4181-4185

[5]

Br?se, 2005, ANGEW CHEM, V117, P8091

[6] Asymmetric conjugate addition of organozinc compounds to α,β-unsaturated aldehydes an ketones with [2.2]paracyclophaneketimine ligands without added copper salts [J].

Bräse, S ;

Höfener, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7879-7881

[7] 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

[8] Multinuclear NMR study of the reactive intermediates in enantioselective epoxidations of allylic alcohols catalyzed by a vanadium complex derived from a planar-chiral hydroxamic acid [J].

Bryliakov, KP ;

Talsi, EP ;

Kühn, T ;

Bolm, C .

NEW JOURNAL OF CHEMISTRY, 2003, 27 (03) :609-614

[9]

CHAUDHARY SK, 1979, TETRAHEDRON LETT, P95

[10] A one-pot multicomponent coupling reaction for the stereocontrolled synthesis of (Z)-trisubstituted allylic alcohols [J].

Chen, YK ;

Walsh, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3702-3703

← 1 2 3 4 5 6 7 →