Asymmetric synthesis of chiral α-ferrocenylalkylamines and their use in the preparation of chiral redox-active receptors

被引：41

作者：

Laurent, P

Miyaji, H

Collinson, SR

Prokes, I

Moody, CJ

Tucker, JHR

Slawin, AMZ

机构：

[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England

[2] Univ St Andrews, Dept Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 23期

关键词：

D O I：

10.1021/ol020162v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new strategy for the asymmetric synthesis of chiral primary alpha-ferrocenylalkylamines has been utilized to generate homochiral redox-active receptors that bind chiral carboxylate anions with moderate enantioselectivity and undergo a redox response to complexation.

引用

收藏

页码：4037 / 4040

页数：4

相关论文

共 29 条

[21] Bis(amidopyridine)-linked calix[4]arenes:: a novel type of receptor for dicarboxylic acids [J].

Miyaji, H ;

Dudic, M ;

Tucker, JHR ;

Prokes, I ;

Light, ME ;

Hursthouse, MB ;

Stibor, I ;

Lhoták, P .

TETRAHEDRON LETTERS, 2002, 43 (05) :873-878

[22] A 'building block' approach to functionalized calix[4]pyrroles [J].

Miyaji, H ;

Sato, W ;

Sessler, JL ;

Lynch, VM .

TETRAHEDRON LETTERS, 2000, 41 (09) :1369-1373

[23] Chiral oxime ethers in asymmetric synthesis.: 3.: Asymmetric synthesis of (R)-N-protected α-amino acids by the addition of organometallic reagents to the ROPHy oxime of cinnamaldehyde [J].

Moody, CJ ;

Gallagher, PT ;

Lightfoot, AP ;

Slawin, AMZ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4419-4425

[24] From enzyme to molecular device. Exploring the interdependence of redox and molecular recognition [J].

Niemz, A ;

Rotello, VM .

ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (01) :44-52

[25] ELECTROCHEMICAL DETECTION OF SACCHARIDES BY THE REDOX CYCLE OF A CHIRAL FERROCENYLBORONIC ACID-DERIVATIVE - A NOVEL METHOD FOR SUGAR SENSING [J].

ORI, A ;

SHINKAI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (17) :1771-1772

[26] Recent advances in the generation of non-racemic ferrocene derivatives and their application to asymmetric synthesis [J].

Richards, CJ ;

Locke, AJ .

TETRAHEDRON-ASYMMETRY, 1998, 9 (14) :2377-2407

[27]

TOGNI A, 1995, FERROCENES HOMOGENEO, pCH4

[28] Electrochemical recognition of cations by bis(pyrrolo)tetrathiafulvalene macrocycles [J].

Trippé, G ;

Levillain, E ;

Le Derf, F ;

Gorgues, A ;

Sallé, M ;

Jeppesen, JO ;

Nielsen, K ;

Becher, J .

ORGANIC LETTERS, 2002, 4 (15) :2461-2464

[29] Recent developments in the redox-switched binding of organic compounds [J].

Tucker, JHR ;

Collinson, SR .

CHEMICAL SOCIETY REVIEWS, 2002, 31 (03) :147-156