Simple protocols for NMR analysis of the enantiomeric purity of chiral primary amines

被引：75

作者：

Perez-Fuertes, Yolanda ^{[1
]}

Kelly, Andrew M. ^{[1
]}

Fossey, John S. ^{[1
]}

Powell, Magdalena E. ^{[1
]}

Bull, Steven D. ^{[1
]}

James, Tony D. ^{[1
]}

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

来源：

NATURE PROTOCOLS | 2008年 / 3卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1038/nprot.2007.524

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

A simple three-component chiral derivatization protocol for determining the enantiopurity of chiral primary amines by H-1 NMR spectroscopic analysis is described here. The method involves condensation of the amines with 2-formylphenylboronic acid and enantiopure 1,1'-bi-2-naphthol. This approach affords a mixture of diastereoisomeric iminoboronate esters whose ratio can be determined by the integration of well-resolved diastereotopic resonances in their H-1 NMR spectra, thus enabling the enantiopurity of the parent amine to be determined easily. The protocol, as described, takes less than 90 min to complete.

引用

页码：210 / 214

页数：5

共 31 条

[11] (S)-2H-2-OXO-5,5-DIMETHYL-4(R)-PHENYL-1,3,2-DIOXAPHOSPHORINANE, A NEW REAGENT FOR THE ENANTIOMERIC EXCESS DETERMINATION OF UNPROTECTED AMINO-ACIDS USING P-31 NMR [J].

HULST, R ;

ZIJLSTRA, RWJ ;

DEVRIES, NK ;

FERINGA, BL .

TETRAHEDRON-ASYMMETRY, 1994, 5 (09) :1701-1710

[12]

James TD, 2002, TOP CURR CHEM, V218, P159

[13] Saccharide-selective boronic acid based Photoinduced Electron Transfer (PET) fluorescent sensors [J].

James, Tony D. .

CREATIVE CHEMICAL SENSOR SYSTEMS, 2007, 277 :107-152

[14] Highly enantioselective hydrogen-transfer reductive amination: Catalytic asymmetric synthesis of primary amines [J].

Kadyrov, R ;

Riermeier, TH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5472-5474

[15] Simple protocol for NMR analysis of the enantiomeric purity of diols [J].

Kelly, AM ;

Pérez-Fuertes, Y ;

Arimori, S ;

Bull, SD ;

James, TD .

ORGANIC LETTERS, 2006, 8 (10) :1971-1974

[16] Powerful chiral phase-transfer catalysts for the asymmetric synthesis of α-alkyl- and α,α,-dialkyl-α-amino acids [J].

Kitamra, M ;

Shirakawa, S ;

Maruoka, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) :1549-1551

[17] Application of the dimenthyl chlorophosphite for the chiral analysis of amines, amino acids and peptides [J].

Kolodiazhnyi, OI ;

Demchuk, OM ;

Gerschkovich, AA .

TETRAHEDRON-ASYMMETRY, 1999, 10 (09) :1729-1732

[18] A new diastereoselective aza-allyl conjugate addition-Michael addition-ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres [J].

Koutsaplis, Magdaline ;

Andrews, Philip C. ;

Bull, Steven D. ;

Duggan, Peter J. ;

Fraser, Benjamin H. ;

Jensen, Paul .

CHEMICAL COMMUNICATIONS, 2007, (34) :3580-3582

[19] Complexation with barium(II) allows the inference of the absolute configuration of primary amines by NMR [J].

López, B ;

Quiñoá, E ;

Riguera, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9724-9725

[20] A practical asymmetric synthesis of homochiral α-arylglycines [J].

Mellin-Morlière, C ;

Aitken, DJ ;

Bull, SD ;

Davies, SG ;

Husson, HP .

TETRAHEDRON-ASYMMETRY, 2001, 12 (01) :149-155

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