The assignment of absolute configuration by NMR

被引:938
作者
Seco, JM
Quiñoá, E
Riguera, R [1 ]
机构
[1] Univ Santiago de Compostela, Dept Quim Inorgan, E-15782 Santiago De Compostela, Spain
[2] Univ Santiago de Compostela, Unidad RMN Biomol, CSIC, E-15782 Santiago De Compostela, Spain
关键词
D O I
10.1021/cr000665j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Different approaches for determining the problem of absolute configuration based on nuclear magnetic resonance (NMR) spectroscopy were studied. The first approach involves those procedures where derivatization of the substrate whose absolute configuration was studied was not necessary. A pure enantiomer was analyzed by NMR in a chiral environment, provided by a chiral solvent or by the addition of a chiral solvating agent (CSA) to a nonchiral standard NMR solvent. Several instrumental methods for the determination of absolute configuration which include X-ray crystallography, chiro-optical methods, optical rotatory dispersion (ORD) or specific optical rotation were also described.
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页码:17 / 117
页数:101
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共 212 条
[1]   Synthesis of dideuterated and enantiomers of monodeuterated tridecanoic acids at C-9 and C-10 positions [J].
Abad, JL ;
Fabriás, G ;
Camps, F .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8582-8588
[2]   NOVEL SPONGE-DERIVED AMINO-ACIDS .11. THE ENTIRE ABSOLUTE STEREOCHEMISTRY OF THE BENGAMIDES [J].
ADAMCZESKI, M ;
QUINOA, E ;
CREWS, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :240-242
[3]   4-deoxyannomontacin and (2,4-cis and trans)-annomontacinone, new bioactive mono-tetrahydrofuran annonaceous acetogenins from Goniothalamus giganteus [J].
Alali, F ;
Zeng, L ;
Zhang, Y ;
Ye, Q ;
Hopp, DC ;
Schwedler, JT ;
McLaughlin, JL .
BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (03) :549-555
[4]   PROTEIN-TYROSINE KINASE INHIBITORY PROPERTIES OF PLANAR POLYCYCLICS OBTAINED FROM THE MARINE SPONGE XESTOSPONGIA CF CARBONARIA AND FROM TOTAL SYNTHESIS [J].
ALVI, KA ;
RODRIGUEZ, J ;
DIAZ, MC ;
MORETTI, R ;
WILHELM, RS ;
LEE, RH ;
SLATE, DL ;
CREWS, P .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4871-4880
[5]   Absolute configuration of some marine metabolites from Cystoseira spp. [J].
Amico, V ;
Piattelli, M ;
Bizzini, M ;
Neri, P .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (11) :1088-1093
[6]   Determination of the enantiomeric purity and the configuration of β-aminoalcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR:: application to β-blockers [J].
Apparu, M ;
Ben Tiba, Y ;
Léo, PM ;
Hamman, S ;
Coulombeau, C .
TETRAHEDRON-ASYMMETRY, 2000, 11 (14) :2885-2898
[7]   Facile and purification free synthesis of Mosher amides utilizing a ROMPgel supported reagent [J].
Arnauld, T ;
Barrett, AGM ;
Hopkins, BT ;
Zécri, FJ .
TETRAHEDRON LETTERS, 2001, 42 (46) :8215-8217
[8]   Trifluoromethyl vs. methyl ability to direct enantioselection in microbial reduction of carbonyl substrates. [J].
Arnone, A ;
Bernardi, R ;
Blasco, F ;
Cardillo, R ;
Resnati, G ;
Gerus, II ;
Kukhar, VP .
TETRAHEDRON, 1998, 54 (12) :2809-2818
[9]  
Augustiniak H, 1996, LIEBIGS ANN, P1657
[10]   Thirteen novel cycloartane-type triterpenes from Combretum quadrangulare [J].
Banskota, AH ;
Tezuka, Y ;
Tran, KQ ;
Tanaka, K ;
Saiki, I ;
Kadota, S .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (01) :57-64