Design, synthesis, and evaluation of conformationally rigid naproxen chiral selectors

Conformationally rigid naproxen chiral selector are designed and synthesized based on our chiral recognition hypothesis. When bonded to silica, this type of chiral selectors of rigid conformation are evaluated chromatographically and demonstrate enhanced enantioselectivity towards naproxen and other members of profens, an important group of non-steroidal anti-inflammatory drugs(NSAIDs). The improved enantioselectivity is believed to stem from a highly preorganized disposition of the key functional groups in this type of chiral selectors, which allow for simultaneous optimal use of hydrogen bonding, π-π face-to-face and face-to-edge interactions with but one enantiomer of naproxen. Strong support for our chiral recognition model is obtained from systematic chromatographic studies as well as a series of $\sp1$H$\{\sp1\rm H\}$ nOe experiments on the 1:1 diastereomeric complexes formed between this type of chiral selector and enantiomers of a naproxen-derived amide.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2011

Author dc:creator

• Liu, Yuelong

Contributors dc:contributor

• Pirkle, William H.

• Chemistry, Organic
• Chemistry, Pharmaceutical

Statement dc:rights

• Copyright 1995 Liu, Yuelong

Language dc:language

eng

Identifier

AAI9543654
(UMI)AAI9543654

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/23400