Enantiodifferentiation of multifunctional tertiary alcohols by NMR spectroscopy with a Whelk-O type chiral solvating agent

被引：21

作者：

Wolf, Christian ^{[1
]}

Cook, Andrea M. ^{[1
]}

Dannatt, Jonathan E. ^{[1
]}

机构：

[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA

来源：

TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 02期

基金：

美国国家科学基金会;

关键词：

NUCLEAR-MAGNETIC-RESONANCE; ENANTIOSELECTIVE NAPROXEN SELECTOR; ABSOLUTE-CONFIGURATION; STATIONARY-PHASE; SHIFT-REAGENT; DERIVATIZING AGENTS; ENANTIOMERIC EXCESSES; DEUTERIUM NMR; ASSIGNMENT; RECOGNITION;

D O I：

10.1016/j.tetasy.2013.11.014

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A Whelk-O type chiral solvating agent (CSA) allows NMR enantioresolution of multifunctional tertiary alcohols. Crystallographic analysis of the CSA revealed two conformers, which can be expected to coexist in solution. One conformation affords a chiral cleft that can engage a single enantiomer in simultaneous hydrogen bonding, pi-pi stacking, and CH/pi interactions. This chiral recognition process yields nonequivalent NMR signals for the enantiomers of eighteen substrates even when substoichiometric amounts of the CSA are used. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：163 / 169

页数：7

共 25 条

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