An enantioselective NMR shift reagent for cationic aromatics

被引:42
作者
Dignam, CF [1 ]
Richards, CJ [1 ]
Zopf, JJ [1 ]
Wacker, LS [1 ]
Wenzel, TJ [1 ]
机构
[1] Bates Coll, Dept Chem, Lewiston, ME 04240 USA
关键词
D O I
10.1021/ol050355t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The water-soluble tetra L-prolinylmethyl derivative of a tetrasulfonated calix[4]resorcarene is an effective chiral NMR solvating agent for compounds with bicyclic aromatic or indole rings. Complexation of bicyclic substrates with the calix[4]resorcarene is likely promoted by hydrophobic effects. The bicyclic substrates have larger association constants with the calix[4]resorcarene than similar phenyl-containing compounds. Substantial enantiomeric discrimination is observed for several resonances in the H-1 NMR spectra of these substrates.
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页码:1773 / 1776
页数:4
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