Enantioselective addition of diethylzinc to aldehydes catalyzed by monosubstituted [2.2]paracyclophane-based N,O-ligands: remarkable cooperative effects of planar and central chiralities

被引：18

作者：

Sugiyama, Shigeo ^{[1
]}

Aoki, Yoshinori ^{[1
]}

Ishii, Keitaro ^{[1
]}

机构：

[1] Meiji Pharmaceut Univ, Dept Med Chem, Tokyo 2048588, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 20期

关键词：

D O I：

10.1016/j.tetasy.2006.10.040

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Diastereomeric monosubstituted [2.2]paracyclophane-based N,O-ligands, which unite the planar and central chiral elements, were optimized for the enantio selective diethylzinc addition to aldehydes. (S)-1-{(S-p)-[2.2]Paracyclophan-4-yl} methyl-2-pyrrolidine-alpha,alpha-diphenylmethanol (S-p,S)-3 catalyzed the addition to give (R)-1-phenyl-l-propanol in a high yield and with a good enantio selectivity (91% ee). (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2847 / 2856

页数：10

共 17 条

[1] 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
CHEMICAL COMMUNICATIONS, 2002, (01) : 26 - 27
[2] The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands
Dahmen, S
Bräse, S
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) : 5940 - 5941
[3] Enantioselective alkynylation of aldehydes catalyzed by [2.2]paracyclophane-based ligands
Dahmen, S
ORGANIC LETTERS, 2004, 6 (13) : 2113 - 2116
[4] Enantioselective Organozinc Addition to Aldehydes Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-Ligands
Kumar, Sundaravel Vivek
Guiry, Patrick J.
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (72)
[5] Efficient synthesis of enantiomerically and diastereomerically pure [2.2]paracyclophane-based N,O-ligands
Rozenberg, VI
Danilova, TI
Sergeeva, EV
Shouklov, IA
Starikova, ZA
Hopf, H
Kühlein, K
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (03) : 432 - 440
[6] [2,2]paracyclophane-based N,O-ligands in alkenylzinc additions to aldehydes
Dahmen, S
Bräse, S
ORGANIC LETTERS, 2001, 3 (25) : 4119 - 4122
[7] Paracyclophanes in Action: Asymmetric Catalytic Dialkylzinc Addition to Imines Using [2.2]Paracyclophane-based N,O-Ligands as Catalysts
Dahmen, Stefan
Braese, Stefan
ISRAEL JOURNAL OF CHEMISTRY, 2012, 52 (1-2) : 139 - 142
[8] Metal-free enantioselective addition of nucleophilic silicon to aromatic aldehydes catalyzed by a [2.2] paracyclophane-based N-heterocyclic carbene catalyst
An, Ping
Huo, Yuwen
Chen, Zhen
Song, Chun
Ma, Yudao
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (15) : 3202 - 3206
[9] Theoretical Approach Towards the Understanding of Asymmetric Additions of Dialkylzinc to Enals and Iminals Catalysed by [2.2]Paracyclophane-Based N,O-Ligands
Kubas, Adam
Braese, Stefan
Fink, Karin
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (27) : 8377 - 8385
[10] Zinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands
Kumar, Sundaravel Vivek
Guiry, Patrick J.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (33)

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