Diastereoselective Lithiation-Substitution of N-Silyl-Protected-(S)-Tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-ones and Applications of Their Derivatives

This thesis describes a method involving the preparation of an L-proline-derived imidazolone protected with an N-triethylsilyl group that undergoes diastereoselective lithiation followed by electrophile quench to give C5-substituted products with syn stereochemistry. The N-silylated derivatives may be more easily N-deprotected as compared to previous N-t-Bu analogues to give secondary ureas. These may serve as precursors to N-phenyl chiral bicyclic guanidines or as NHC precursors for synthesis of corresponding complexes.

Name thesis:degree_name

M.Sc. Chemistry

Level thesis:degree_level

Masters

Discipline thesis:degree_discipline

Faculty of Mathematics and Science

Department dc:contributor.department

Department of Chemistry

Grantor

Brock University

Year dc:date.issued

2014

Author dc:creator

• Sadraei, Seyed Iraj

• L-proline-derived
• imidazolone protected
• diastereoselective lithiation
• chiral guanidines
• N-heterocyclic carbene complexes

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/10464/5696

OAI identifier oai:identifier

oai:brocku.scholaris.ca:10464/5696