Simultaneous Chirality Sensing of Multiple Amines by 19F NMR

被引:136
作者
Zhao, Yanchuan [1 ]
Swager, Timothy M. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
COUPLED CIRCULAR-DICHROISM; NEUTRAL ORGANIC-COMPOUNDS; ENANTIOMERIC EXCESS; ABSOLUTE-CONFIGURATION; SOLVATING AGENTS; CONFORMATIONAL STABILIZER; MOSHER AMIDES; HYDROXY-ACIDS; SPECTROSCOPY; COMPLEXES;
D O I
10.1021/jacs.5b00556
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The rapid, detection and differentiation of chiral compounds is important to synthetic, medicinal, and biological chemistry. Palladium complexes : with chiral pincer ligands are demonstrated to have utility in determining the chirality of various amines. The binding of enantiomeric amines induces distinct F-19 NMR. shifts of the fluorine atoms appended on the ligand that,defines a Chiral environment around 1:palladium. It is further demonstrated that this method has the ability to evaluate the enantiomeric composition and discriminate between enantiomers with chiral centers several carbons away from the binding site. The wide detection window provided by optimized chiral chemosensors allows the simultaneous identification of as many as 12 chiral amines. The extraordinary discriminating ability of this method is demonstrated by the resolution of chiral aliphatic amines that are difficult to separate using,chiral chromatography:
引用
收藏
页码:3221 / 3224
页数:4
相关论文
共 43 条
[11]   Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons [J].
Hoye, Thomas R. ;
Jeffrey, Christopher S. ;
Shao, Feng .
NATURE PROTOCOLS, 2007, 2 (10) :2451-2458
[12]   MTPA (Mosher) amides of cyclic secondary amines: Conformational aspects and a useful method for assignment of amine configuration [J].
Hoye, TR ;
Renner, MK .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2056-2064
[13]   Rapid Optical Methods for Enantiomeric Excess Analysis: From Enantioselective Indicator Displacement Assays to Exciton-Coupled Circular Dichroism [J].
Jo, Hyun Hwa ;
Lin, Chung-Yon ;
Anslyn, Eric V. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (07) :2212-2221
[14]   Rapid determination of enantiomeric excess: a focus on optical approaches [J].
Leung, Diana ;
Kang, Sung Ok ;
Anslyn, Eric V. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) :448-479
[15]   Chiral Solvating Agents for Cyanohydrins and Carboxylic Acids [J].
Moon, Lomary S. ;
Pal, Mohan ;
Kasetti, Yoganjaneyulu ;
Bharatam, Prasad V. ;
Jolly, Ravinder S. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (16) :5487-5498
[16]   A novel heterobimetallic complex composed of the imide-bridged [3]ferrocenophane and the tridentate palladium(II) complex [J].
Moriuchi, T ;
Bandoh, S ;
Miyaji, Y ;
Hirao, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 599 (02) :135-142
[17]  
Moriuchi T, 2000, CHEM LETT, P148
[18]   NMR DETERMINATION OF ENANTIOMERIC PURITY [J].
PARKER, D .
CHEMICAL REVIEWS, 1991, 91 (07) :1441-1457
[19]   13C NMR Spectroscopy for the Differentiation of Enantiomers Using Chiral Solvating Agents [J].
Perez-Trujillo, Miriam ;
Monteagudo, Eva ;
Parella, Teodor .
ANALYTICAL CHEMISTRY, 2013, 85 (22) :10887-10894
[20]   "NMR Chemosensing" Using Monolayer-Protected Nanoparticles as Receptors [J].
Perrone, Barbara ;
Springhetti, Sara ;
Ramadori, Federico ;
Rastrelli, Federico ;
Mancin, Fabrizio .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) :11768-11771