Simple protocol for NMR analysis of the enantiomeric purity of diols

被引:75
作者
Kelly, AM [1 ]
Pérez-Fuertes, Y [1 ]
Arimori, S [1 ]
Bull, SD [1 ]
James, TD [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
关键词
D O I
10.1021/ol0602351
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral 1,2-, 1,3-, and 1,4-diols by H-1 NMR spectroscopic analysis is described. The method involves treatment with 2-formylphenylboronic acid and enantiopure alpha-methylbenzylamine to afford a mixture of diastereolsomeric iminoboronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diol.
引用
收藏
页码:1971 / 1974
页数:4
相关论文
共 21 条
[1]   A NEW P-31 NMR METHOD FOR THE ENANTIOMERIC EXCESS DETERMINATION OF DIOLS AND SECONDARY DIAMINES WITH C-2 SYMMETRY [J].
BRUNEL, JM ;
FAURE, B .
TETRAHEDRON-ASYMMETRY, 1995, 6 (09) :2353-2356
[2]   A REAGENT FOR DETERMINING OPTICAL PURITIES OF DIOLS BY FORMATION OF DIASTEREOMERIC ARYLBORONATE ESTERS [J].
BURGESS, K ;
PORTE, AM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (11) :1182-1184
[3]   (S)-(+)-N-acetylphenylglycineboronic acid:: A chiral derivatizing agent for Ee determination of 1,2-diols [J].
Caselli, E ;
Danieli, C ;
Morandi, S ;
Bonfiglio, B ;
Forni, A ;
Prati, F .
ORGANIC LETTERS, 2003, 5 (25) :4863-4866
[4]  
CHALLENGER AC, 2001, CHIRAL INTERMEDIATES
[5]   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
[6]   The assignment of the absolute configuration of 1,2-diols by low-temperature NMR of a single MPA derivative [J].
Freire, F ;
Seco, JM ;
Quiñoá, E ;
Riguera, R .
ORGANIC LETTERS, 2005, 7 (22) :4855-4858
[7]   Determining the absolute stereochemistry of secondary/secondary diols by 1H NMR:: Basis and applications [J].
Freire, F ;
Seco, JM ;
Quiñoá, E ;
Riguera, R .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3778-3790
[8]   NMR determination of the absolute configuration of chiral 1,2-and 1,3-diols [J].
Fukui, H ;
Fukushi, Y ;
Tahara, S .
TETRAHEDRON LETTERS, 2003, 44 (21) :4063-4065
[9]   Menthyldichlorophosphate: A chiral derivatizing agent for symmetrical diols [J].
Garner, CM ;
McWhorter, C ;
Goerke, AR .
TETRAHEDRON LETTERS, 1997, 38 (44) :7717-7720
[10]  
Hanessian S., 1983, TOTAL SYNTHESIS NATU