Mix and shake method for configurational assignment by NMR:: Application to chiral amines and alcohols

被引：43

作者：

Porto, S

Durán, J

Seco, JM

Quiñoá, E

Riguera, R ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Dept Quim Organ, E-15782 Santiago De Compostela, Spain

[2] Univ Santiago de Compostela, CSIC, Biomol Asociada, Unidad RMN, E-15782 Santiago De Compostela, Spain

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 17期

关键词：

D O I：

10.1021/ol034853i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic A new methodology for determining absolute configurations by NMR in just a few minutes is presented. The required derivatives are obtained by mixing a solid matrix-bound auxiliary reagent (MPA, MTPA, or BPG) with the chiral substrate (primary amines or secondary alcohols) directly in the NMR tube. The NMR spectra of the derivatives are obtained without any type of separation, workup, or manipulation. The use of a 1:2 (R)/(S)-MPA resin permits the configurational assignment to be carried out with just one spectrum.

引用

收藏

页码：2979 / 2982

页数：4

相关论文

共 15 条

[1] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[2] Absolute configuration of secondary alcohols by 1H-NMR:: In situ complexation of α-methoxyphenylacetic acid esters with barium(II) [J].

Garcia, R ;

Seco, JM ;

Vázquez, SA ;

Quiñoá, E ;

Riguera, R .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4579-4589

[3] CONFORMATIONAL STRUCTURE AND DYNAMICS OF ARYLMETHOXYACETATES - DNMR SPECTROSCOPY AND AROMATIC SHIELDING EFFECT [J].

LATYPOV, SK ;

SECO, JM ;

QUINOA, E ;

RIGUERA, R .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :504-515

[4] Assignment of the absolute configuration of β-chiral primary alcohols by NMR:: Scope and limitations [J].

Latypov, SK ;

Ferreiro, MJ ;

Quiñoá, E ;

Riguera, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4741-4751

[5] DETERMINATION OF THE ABSOLUTE STEREOCHEMISTRY OF CHIRAL AMINES BY H-1-NMR OF ARYLMETHOXYACETIC ACID-AMIDES - THE CONFORMATIONAL MODEL [J].

LATYPOV, SK ;

SECO, JM ;

QUINOA, E ;

RIGUERA, R .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1538-1545

[6] Are both the (R)- and the (S)-MPA esters really needed for the assignment of the absolute configuration of secondary alcohols by NMR?: The use of a single derivative [J].

Latypov, SK ;

Seco, JM ;

Quiñoá, E ;

Riguera, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (05) :877-882

[7] 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

[8] Absolute configuration of 1,n-diols by NMR:: The importance of the combined anisotropic effects in bis-arylmethoxyacetates [J].

Seco, JM ;

Martino, M ;

Quiñoá, E ;

Riguera, R .

ORGANIC LETTERS, 2000, 2 (21) :3261-3264

[9] Determining factors in the assignment of the absolute configuration of alcohols by NMR. The use of anisotropic effects on remote positions. [J].

Seco, JM ;

Latypov, SK ;

Quinoa, E ;

Riguera, R .

TETRAHEDRON, 1997, 53 (25) :8541-8564

[10] Simultaneous enantioresolution and assignment of absolute configuration of secondary alcohols by directly coupled HPLC-NMR of 9-AMA esters [J].

Seco, JM ;

Tseng, LH ;

Godejohann, M ;

Quiñoá, E ;

Riguera, R .

TETRAHEDRON-ASYMMETRY, 2002, 13 (19) :2149-2153