Interplay between the diamine structure and absolute helicity in Ni-salen metallofoldamers

被引：19

作者：

Dong, Zhenzhen ^{[1
]}

Bai, Shi ^{[1
]}

Yap, Glenn P. A. ^{[1
]}

Fox, Joseph M. ^{[1
]}

机构：

[1] Univ Delaware, Brown Labs, Dept Chem & Biochem, Newark, DE 19803 USA

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 13期

关键词：

SITE-SELECTIVE TRANSMETALATION; DIELS-ALDER REACTIONS; ASYMMETRIC EPOXIDATION; (SALEN)MANGANESE(III) COMPLEX; ABIOTIC METALLOFOLDAMERS; SECONDARY STRUCTURE; LIGAND; CATALYST; METAL; TRANS-CYCLOHEXANE-1,2-DIAMINE;

D O I：

10.1039/c0cc04794e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The nature of internal chiral diamines can greatly influence the ratio of helical diastereomers for Ni-salen based metallofoldamers. The diastereomer ratio is small for metallofoldamers derived from (1R, 2R)-cyclohexanediamine, (11R, 12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-diamine, or (1R, 2R)-cyclopentanediamine. By contrast, the foldamer from (1S, 2S)-1,2-diphenylethylenediamine provides a relatively large bias (6 : 1) for the P-helical diastereomer as evidenced by NMR studies, chiroptical data, and X-ray studies. A model is proposed to explain the origin of the helical bias. These findings underscore the need to consider helical diastereomers in models for asymmetric induction in metal-salen catalyzed reactions.

引用

页码：3781 / 3783

页数：3

共 49 条

[1] Ca2+- and Ba2+-selective receptors based on site-selective transmetalation of multinuclear polyoxime-zinc(II) complexes [J].

Akine, S ;

Taniguchi, T ;

Saiki, T ;

Nabeshima, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) :540-541

[2] Novel synthetic approach to trinuclear 3d-4f complexes: Specific exchange of the central metal of a trinuclear zinc(II) complex of a tetraoxime ligand with a lanthanide(III) ion [J].

Akine, S ;

Taniguchi, T ;

Nabeshima, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4670-4673

[3] Acyclic bis(N2O2 chelate) ligand for trinuclear d-block homo- and heterometal complexes [J].

Akine, Shigehisa ;

Taniguchi, Takanori ;

Nabeshima, Tatsuya .

INORGANIC CHEMISTRY, 2008, 47 (08) :3255-3264

[4] Chiral single-stranded metallohelix: metal-mediated folding of linear oligooxime ligand [J].

Akine, Shigehisa ;

Taniguchi, Takanori ;

Nabeshima, Tatsuya .

TETRAHEDRON LETTERS, 2006, 47 (47) :8419-8422

[5] Helical metallohost-guest complexes via site-selective transmetalation of homotrinuclear complexes [J].

Akine, Shigehisa ;

Taniguchi, Takanori ;

Nabeshima, Tatsuya .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) :15765-15774

[6] Multiple Folding Structures Mediated by Metal Coordination of Acyclic Multidentate Ligand [J].

Akine, Shigehisa ;

Morita, Yoko ;

Utsuno, Fumihiko ;

Nabeshima, Tatsuya .

INORGANIC CHEMISTRY, 2009, 48 (22) :10670-10678

[7] Stereoselective recognition of an aziridine with a Co(III) complex: A potential transition-state analogue for catalytic epoxidation [J].

Bobb, R ;

Alhakimi, G ;

Studnicki, L ;

Lough, A ;

Chin, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (17) :4544-4545

[8] Origin of the asymmetric induction in metallosalen-catalyzed reactions of aldehydes [J].

Chaladaj, Wojciech ;

Jurczak, Janusz .

CHEMICAL COMMUNICATIONS, 2009, (44) :6747-6749

[9] A NEAR-PLANAR PENTADENTATE SILVER(I) COMPLEX - THE CRYSTAL AND MOLECULAR-STRUCTURE OF (2,2'-6',2'-6'',2'''-6''',2''''-QUINQUEPYRIDINE)SILVER(I) HEXAFLUOROPHOSPHATE [J].

CONSTABLE, EC ;

DREW, MGB ;

FORSYTH, G ;

WARD, MD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (22) :1450-1451

[10] OLIGOPYRIDINES AS HELICATING LIGANDS [J].

CONSTABLE, EC .

TETRAHEDRON, 1992, 48 (46) :10013-10059

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