DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF CHIRAL SECONDARY ALCOHOLS - NEW ADVANCES USING C-13-NMR AND 2D-NMR SPECTROSCOPY

被引:35
作者
PEHK, T
LIPPMAA, E
LOPP, M
PAJU, A
BORER, BC
TAYLOR, RJK
机构
[1] TALLINN CHEM INST,TALLINN 0108,ESTONIA
[2] UNIV E ANGLIA,SCH CHEM SCI,NORWICH NR4 7TJ,NORFOLK,ENGLAND
关键词
D O I
10.1016/S0957-4166(00)80354-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The use of H-1-C-13 and H-1-H-1 2D COSY correlation experiments substantially enhances the potential of the NMR procedure for determining the absolute configuration of chiral secondary alcohols via their diastereomeric MPA and/or MTPA esters. Phenyl ring current effects are observed over remarkably long distances and comparable effects are seen for both C-13 and H-1 chemical shifts. The use of C-13 chemical shifts to aid configurational assignment is particularly valuable.
引用
收藏
页码:1527 / 1532
页数:6
相关论文
共 17 条
[1]   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
[2]  
BORER BC, 1992, SYNLETT, P117
[3]  
COREY EJ, 1972, J AM CHEM SOC, V94, P2506
[4]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[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]   REGIOSPECIFIC EPOXIDE OPENING WITH ACETYLENIC ALANES - IMPROVED TOTAL SYNTHESIS OF E AND F PROSTAGLANDINS [J].
FRIED, J ;
LIN, CH ;
DALVEN, P ;
SIH, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (12) :4343-&
[7]   ABSOLUTE-CONFIGURATIONS OF CYTO-TOXIC MARINE CEMBRANOLIDES - CONSIDERATION OF MOSHERS METHOD [J].
KUSUMI, T ;
OHTANI, I ;
INOUYE, Y ;
KAKISAWA, H .
TETRAHEDRON LETTERS, 1988, 29 (37) :4731-4734
[8]   SYNTHESIS OF A NOVEL 4-CARBON CHIRON - (R)-1-TERT-BUTYLDIMETHYLSILYL-3,4-EPOXY-BUT-1-YNE [J].
LOPP, M ;
KANGER, T ;
MURAUS, A ;
PEKH, T ;
LILLE, U .
TETRAHEDRON-ASYMMETRY, 1991, 2 (10) :943-944
[9]  
NIIDAS P, 1989, P ESTONIAN ACAD SCI, V38, P285
[10]   ABSOLUTE-CONFIGURATIONS OF MARINE DITERPENES POSSESSING A XENICANE SKELETON - AN APPLICATION OF AN ADVANCED MOSHER METHOD [J].
OHTANI, I ;
KUSUMI, T ;
ISHITSUKA, MO ;
KAKISAWA, H .
TETRAHEDRON LETTERS, 1989, 30 (24) :3147-3150