Optical resolution of N-(t-butoxycarbonyl) leucine through mixed ligand complex formation with (R)-N-(2-pyridylmethyl)pipecolatocopper(II)

被引：0

作者：

Yajima, Tatsuo ^{[1
]}

Fukushima, Takeo ^{[1
]}

Yamada, Atsuya ^{[1
]}

Shiraiwa, Tadashi ^{[1
]}

机构：

[1] Kansai Univ, Fac Chem Mat & Bioengn, Yamate Cho, Suita, Osaka 5648680, Japan

来源：

INORGANICA CHIMICA ACTA | 2017年 / 466卷

基金：

日本学术振兴会;

关键词：

Optical resolution; N-protected amino acid; Mixed ligand complex; Copper(II); ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; METAL;

D O I：

10.1016/j.ica.2017.06.052

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A copper(II) complex of (R)-N-(2-pyridylmethyl) pipecolate (pmpi) was prepared, and its structure was revealed by X-ray crystal structure analysis. Mixed ligand complexes were then prepared from this complex and (R)- and (S)-N-(t-butoxycarbonyl) leucinate (BocLeu). The (R)-BocLeu complex is less soluble in aqueous acetonitrile and more soluble in acetone than the (S)-BocLeu complex, and the reason was discussed on the basis of their structures. Recrystallization of the reaction mixture consisting of Cu(II) ion, pmpi, and (RS)-BocLeu from aqueous acetonitrile gave the (R)-BocLeu complex and that from acetone gave the (S)-BocLeu complex. (C) 2017 Elsevier B.V. All rights reserved.

引用

页码：451 / 455

页数：5

共 9 条

[1] Influence of the metal and chiral diamine on metal(II)salen catalysed, asymmetric synthesis of α-methyl α-amino acids [J].

Belokon, YN ;

Fuentes, J ;

North, M ;

Steed, JW .

TETRAHEDRON, 2004, 60 (14) :3191-3204

[2] Chiral salen-metal complexes as novel catalysts for the asymmetric synthesis of α-amino acids under phase transfer catalysis conditions [J].

Belokon, YN ;

North, M ;

Churkina, TD ;

Ikonnikov, NS ;

Maleev, VI .

TETRAHEDRON, 2001, 57 (13) :2491-2498

[3] IL MILIONE:: a suite of computer programs for crystal structure solution of proteins [J].

Burla, Maria C. ;

Caliandro, Rocco ;

Camalli, Mercedes ;

Carrozzini, Benedetta ;

Cascarano, Giovanni L. ;

De Caro, Liberato ;

Giacovazzo, Carmelo ;

Polidori, Giampiero ;

Siliqi, Dritan ;

Spagna, Riccardo .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2007, 40 :609-613

[4] STEREOCHEMISTRY AND REACTIVITY OF METAL-SCHIFF BASE COMPLEXES .2. HIGH STEREOSELECTIVITY IN (1S,2S)-N,N'-1,2-CYCLOHEXYLENEBIS-(SALICYLIDENEAMINATO)(SAL2-(S,S)-CHXN) COBALT(III) COMPLEXES WITH AMINO-ACIDS AND OPTICAL RESOLUTION OF AMINO-ACIDS WITH COBALT(III)-SAL2-(S,S)-CHXN [J].

FUJII, Y ;

SANO, M ;

NAKANO, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (10) :2609-2614

[5] A short history of SHELX [J].

Sheldrick, George M. .

ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 :112-122

[6] Adenosine 5′-triphosphate (ATp4-):: Aspects of the coordination chemistry of a multitalented biological substrate [J].

Sigel, H .

PURE AND APPLIED CHEMISTRY, 2004, 76 (02) :375-388

[7] Optical Resolution of -Amino Acids by Reverse Osmosis using Enantioselective Polymer Membrane Containing Chiral Metal-Schiff Base Complex [J].

Singh, Kripal ;

Ingole, Pravin G. ;

Bajaj, H. C. ;

Bhattacharya, Amit ;

Brahmbhatt, Harshad R. .

SEPARATION SCIENCE AND TECHNOLOGY, 2010, 45 (10) :1374-1384

[8] Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases; Part 1: alkyl halide alkylations [J].

Sorochinsky, Alexander E. ;

Luis Acena, Jose ;

Moriwaki, Hiroki ;

Sato, Tatsunori ;

Soloshonok, Vadim A. .

AMINO ACIDS, 2013, 45 (04) :691-718

[9] Metal ion-assisted weak interactions involving biological molecules. From small complexes to metalloproteins [J].

Yamauchi, O ;

Odani, A ;

Hirota, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2001, 74 (09) :1525-1545

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