The Design and Utility of Chiral Derivatizing Agents

A variety of chloroformates derived from aryl perfluoroalkyl secondary carbinols were utilized as chiral derivatizing agents for asymmetric primary amines, secondary alcohols and several primary carbinols. The chromatographic behavior and nuclear magnetic resonance properties of selected diastereomeric carbamates and carbonates derived from several chloroformates and a number of amines and alcohols are reported. Several chloroformates exhibited favorable properties as manifested by the facile chromatographic separation of a number of derived diastereomeric carbamates, and a discussion of the reasons underlying enhanced chromatographic resolution of carbamate diastereomers is presented. In addition, several chloroformates were effectively applied as NMR chiral derivatizing agents in a manner that allowed for the convenient determination of enantiomeric purity and absolute configuration of various asymmetric primary amines and secondary carbinols. The resolution and assignment of absolute configuration of several chiral chloroformates is presented along with a discussion of the enhanced stability of chloroformates derived from aryl perfluoroalkyl secondary alcohols.

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

2014

Author dc:creator

• Robertson, Michael Wayne

• Chemistry, Organic

Language dc:language

eng

Identifier

(UMI)AAI8127679

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/67282