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Heptakis[2,3‐di‐ O ‐methyl‐6‐ O ‐( L ‐valine‐ tert ‐butylamide‐ N α ‐ylcarbonylmethyl)]‐β‐cyclodextrin: a New Multifunctional Cyclodextrin CSA for the NMR Enantiodiscrimination of Polar and Apolar Substrates
Author(s) -
UccelloBarretta Gloria,
Nazzi Samuele,
Balzano Federica,
Levkin Pavel A.,
Schurig Volker,
Salvadori Piero
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700018
Subject(s) - chemistry , valine , cyclodextrin , stereochemistry , nuclear magnetic resonance spectroscopy , enantiomer , medicinal chemistry , amino acid , organic chemistry , biochemistry
Heptakis[2,3‐di‐ O ‐methyl‐6‐ O ‐( L ‐valine‐ tert ‐butylamide‐ N α ‐ylcarbonylmethyl)]‐β‐cyclodextrin with methyl groups on the secondary sites and a diamide chiral selector on the primary ones showed considerable utility as a CSA in the NMR enantiodiscrimination of a wide spectrum of amino acid derivatives, while also allowing trisubstituted allenes to be enantiodiscriminated. Enantiodiscrimination processes were investigated by Diffusion‐Ordered SpectroscopY (DOSY). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)