AN IMPROVED SYNTHESIS OF CHIRAL OXAZOLIDINE-2-SELONES - HIGHLY SENSITIVE SE-77 NMR REAGENTS FOR THE DETECTION AND QUANTITATION OF CHIRALITY

被引:45
作者
SILKS, LA
PENG, J
ODOM, JD
DUNLAP, RB
机构
[1] Los Alamos National Laboratory, Biochemistry Section and Stable Isotope Resource, INC-4 MS C-346, Los Alamos
[2] Department of Chemistry and Biochemistry, University of South Carolina, Columbia
关键词
D O I
10.1021/jo00024a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the title compounds from readily available oxazolines has been accomplished in one step in high yield. These chiral reagents exhibit extraordinary Se-77 chemical shift sensitivity and are useful for the detection and quantitation of chirality at remotely disposed chiral centers.
引用
收藏
页码:6733 / 6736
页数:4
相关论文
共 47 条
[1]   A NEW REAGENT FOR A VERY SIMPLE AND EFFICIENT DETERMINATION OF ENANTIOMERIC PURITY OF ALCOHOLS BY P-31 NMR [J].
ALEXAKIS, A ;
MUTTI, S ;
NORMANT, JF ;
MANGENEY, P .
TETRAHEDRON-ASYMMETRY, 1990, 1 (07) :437-440
[2]   THE REACTION OF PARA-TOLYL ISOSELENOCYANATE WITH PRIMARY AND SECONDARY-AMINES - A MULTINUCLEAR MAGNETIC-RESONANCE STUDY [J].
BOCCANFUSO, AM ;
GRIFFIN, DW ;
DUNLAP, RB ;
ODOM, JD .
BIOORGANIC CHEMISTRY, 1989, 17 (02) :231-239
[3]   INTRAMOLECULAR ACYL RADICAL ALKENE ADDITION-REACTIONS - MACROCYCLIZATION REACTIONS [J].
BOGER, DL ;
MATHVINK, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4008-4011
[4]   STEREOCHEMICAL ANALYSIS OF A QUASISYMMETRICAL DIALKYL SULFOXIDE OBTAINED BY A DIVERTED BIODEHYDROGENATION REACTION [J].
BUIST, PH ;
MARECAK, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5877-5878
[5]   SE-77 NMR-STUDIES OF SOME ORGANOSELENIUM COMPOUNDS CONTAINING CARBON-SELENIUM DOUBLE-BONDS [J].
CULLEN, ER ;
GUZIEC, FS ;
MURPHY, CJ ;
WONG, TC ;
ANDERSEN, KK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (24) :7055-7057
[6]   C-13 NUCLEAR MAGNETIC-RESONANCE STUDIES OF SOME ORGANOSELENIUM COMPOUNDS CONTAINING CARBON-SELENIUM DOUBLE-BONDS [J].
CULLEN, ER ;
GUZIEC, FS ;
MURPHY, CJ ;
WONG, TC ;
ANDERSEN, KK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (04) :473-476
[7]   DYNAMIC SE-77 NMR OF PHENYLSELENYL CYCLOHEXANE DERIVATIVES [J].
DUDDECK, H ;
WAGNER, P ;
GEGNER, S .
TETRAHEDRON LETTERS, 1985, 26 (09) :1205-1208
[8]   MAGNETIC-RESONANCE STUDIES OF SELENIUM CONTAINING COMPOUNDS [J].
DUNLAP, RB ;
ODOM, JD .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1988, 38 (3-4) :217-229
[9]   CHIRAL SEPARATION OF HETEROCYCLIC DRUGS BY HPLC - SOLUTE STATIONARY PHASE BASE-PAIR INTERACTIONS [J].
FEIBUSH, B ;
FIGUEROA, A ;
CHARLES, R ;
ONAN, KD ;
FEIBUSH, P ;
KARGER, BL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3310-3318
[10]  
GETTINS P, 1991, J BIOL CHEM, V266, P3422