Chemical deracemization and (S) to (R) interconversion of some fluorine-containing α-amino acids

被引：40

作者：

Sorochinsky, Alexander E. ^{[1
,2
,3
]}

Ueki, Hisanori ^{[4
]}

Luis Acena, Jose ^{[1
]}

Ellis, Trevor K. ^{[5
]}

Moriwaki, Hiroki ^{[6
]}

Sato, Tatsunori ^{[6
]}

Soloshonok, Vadim A. ^{[1
,2
]}

机构：

[1] Univ Basque Country UPV EHU, Dept Organ Chem 1, Fac Chem, San Sebastian 20018, Spain

[2] Basque Fdn Sci, IKERBASQUE, Bilbao 48011, Spain

[3] Natl Acad Sci Ukraine, Inst Bioorgan Chem & Petrochem, UA-02660 Kiev, Ukraine

[4] Natl Inst Mat Sci, Int Ctr Mat Nanoarchitecton MANA, Tsukuba, Ibaraki 3050044, Japan

[5] Dept Chem & Phys, Weatherford, OK 73096 USA

[6] Hamari Chem Ltd, Higashi Yodogawa Ku, Osaka 5330024, Japan

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2013年 / 152卷

关键词：

Chiral recognition; Deracemization; D-(R)-amino acids; Resolution; Diastereoselectivity; Asymmetric induction; NUCLEOPHILIC GLYCINE EQUIVALENTS; MICHAEL ADDITION-REACTIONS; SCALE ASYMMETRIC-SYNTHESIS; VIRTUALLY COMPLETE CONTROL; FACE DIASTEREOSELECTIVITY; SELF-DISPROPORTIONATION; EFFICIENT SYNTHESIS; ENANTIOPURE COMPOUNDS; CHIRAL EQUIVALENTS; ENANTIOMERS;

D O I：

10.1016/j.jfluchem.2013.02.022

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Several omega-CF3-substituted alpha-amino acids have been prepared in optically pure form via two complementary approaches. Racemic fluorinated derivatives of 2-aminobutanoic acid, norvaline and norleucine were chemically deracemized by complexation with a Ni(II) salt and a chiral reagent derived from alpha-(phenyl)ethylamine. Additionally this procedure also allowed the conversion of readily available L-amino acids, CF3-analogs of cysteine and methionine, into the corresponding unnatural D-series. Optically pure amino acids are obtained upon disassembly of the Ni(II) complexes with recovery of the chiral ligand. (C) 2013 Elsevier B.V. All rights reserved.

引用

页码：114 / 118

页数：5

共 42 条

[1] SPECIFICATION OF MOLECULAR CHIRALITY [J].

CAHN, RS ;

INGOLD, C ;

PRELOG, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (04) :385-&

[2] THE SPECIFICATION OF ASYMMETRIC CONFIGURATION IN ORGANIC CHEMISTRY [J].

CAHN, RS ;

INGOLD, CK ;

PRELOG, V .

EXPERIENTIA, 1956, 12 (03) :81-94

[3] Nucleophilic addition of 3,3,3-trifluoropropynyllithium to D-glyceraldimine: Concise synthesis of both enantiomers of 5,5,5-trifluoronorvaline [J].

Chen, Qi ;

Qiu, Xiao-Long ;

Qing, Feng-Ling .

JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (10) :1182-1186

[4] Design and synthesis of a new generation of 'NH'-Ni(II) complexes of glycine Schiff bases and their unprecedented C-H vs. N-H chemoselectivity in alkyl halide alkylations and Michael addition reactions [J].

Ellis, TK ;

Soloshonok, VA .

SYNLETT, 2006, (04) :533-538

[5] New generation of nucleophilic glycine equivalents [J].

Ellis, TK ;

Ueki, H ;

Soloshonok, VA .

TETRAHEDRON LETTERS, 2005, 46 (06) :941-944

[6] Efficient synthesis of 2-aminoindane-2-carboxylic acid via dialkylation of nucleophilic glycine equivalent [J].

Ellis, TK ;

Hochla, VM ;

Soloshonok, VA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4973-4976

[7] Efficient synthesis of sterically constrained symmetrically α,α-disubstituted α-amino acids under operationally convenient conditions [J].

Ellis, TK ;

Martin, CH ;

Tsai, GM ;

Ueki, H ;

Soloshonok, VA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6208-6214

[8] Design, synthesis, and evaluation of a new generation of modular nucleophilic glycine equivalents for the efficient synthesis of sterically constrained α-amino acids [J].

Ellis, Trevor K. ;

Ueki, Hisanori ;

Yamada, Takeshi ;

Ohfune, Yasufumi ;

Soloshonok, Vadim A. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) :8572-8578

[9] LIGAND-EXCHANGE CHROMATOGRAPHY OF ALPHA-TRIFLUOROMETHYL-ALPHA-AMINO ACIDS ON CHIRAL SORBENTS [J].

GALUSHKO, SV ;

SHISHKINA, IP ;

SOLOSHONOK, VA ;

KUKHAR, VP .

JOURNAL OF CHROMATOGRAPHY, 1990, 511 :115-121

[10] FACILE SYNTHESIS OF FLUORINATED METHIONINES [J].

HOUSTON, ME ;

HONEK, JF .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (12) :761-762

← 1 2 3 4 5 →