Novel chiral tridentate Schiff base ligands of the [2.2]paracyclophane series:: synthesis and application

被引：47

作者：

Danilova, TI

Rozenberg, VI

Sergeeva, EV

Starikova, ZA

Bräse, S

机构：

[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

[2] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 14期

基金：

俄罗斯基础研究基金会;

关键词：

D O I：

10.1016/S0957-4166(03)00326-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first example of the efficient application of chiral tridentate N,O-[2.2]paracyclophane ligands of the imino type for enantioselective diethylzinc addition to aliphatic and aromatic aldehydes is presented. The enantiomeric excess of the resulted secondary alcohols is LIP to 93% e.e. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：2013 / 2019

页数：7

共 30 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
ANTONOV, DY
BELOKON, YN
IKONNIKOV, NS
ORLOVA, SA
PISAREVSKY, AP
RAEVSKI, NI
ROZENBERG, VI
SERGEEVA, EV
STRUCHKOV, YT
TARAROV, VI
VORONTSOV, EV
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (14): : 1873 - 1879
[2] ARATANI T, 1975, TETRAHEDRON LETT, P1707
[3] Highly diastereoselective pinacol coupling of aldehydes catalyzed by titanium Schiff base complexes
Bandini, M
Cozzi, PG
Morganti, S
Umani-Ronchi, A
[J]. TETRAHEDRON LETTERS, 1999, 40 (10) : 1997 - 2000
[4] 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
Belokon, Y
Moscalenko, M
Ikonnikov, N
Yashkina, L
Antonov, D
Vorontsov, E
Rozenberg, V
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (19) : 3245 - 3250
[5] Enantioselective pinacol coupling of aldehydes mediated and catalyzed by chiral titanium complexes
Bensari, A
Renaud, JL
Riant, O
[J]. ORGANIC LETTERS, 2001, 3 (24) : 3863 - 3865
[6] Utilisation of homogeneous and supported chiral metal(salen) complexes in asymmetric catalysis
Canali, L
Sherrington, DC
[J]. CHEMICAL SOCIETY REVIEWS, 1999, 28 (02) : 85 - 93
[7] Enantioselective addition of Et(2)Zn to aldehydes promoted by a chiral Schiff base metal complex
Cozzi, PG
Papa, A
UmaniRonchi, A
[J]. TETRAHEDRON LETTERS, 1996, 37 (26) : 4613 - 4616
[8] The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands
Dahmen, S
Bräse, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) : 5940 - 5941
[9] Planar and central chiral [2.2] paracyclophane-based N,O-ligands as highly active catalysts in the diethylzinc addition to aldehydes
Dahmen, S
Bräse, S
[J]. CHEMICAL COMMUNICATIONS, 2002, (01) : 26 - 27
[10] Preparation of planar chiral amino phenols based on the [2.2]paracyclophane backbone
Dahmen, S
Bräse, S
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (20) : 2845 - 2850

← 1 2 3 →