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


Autoria(s): Sadraei, Seyed Iraj
Contribuinte(s)

Department of Chemistry

Data(s)

10/09/2014

10/09/2014

10/09/2014

Resumo

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.

Identificador

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

Idioma(s)

eng

Publicador

Brock University

Palavras-Chave #L-proline-derived #imidazolone protected #diastereoselective lithiation #chiral guanidines #N-heterocyclic carbene complexes
Tipo

Electronic Thesis or Dissertation