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Paper | Special issue | Vol 88, No. 1, 2014, pp.347-362
Published online, 8th July, 2013
DOI: 10.3987/COM-13-S(S)29
Diastereoselective Lithiation of N-Silyl-Protected (S)-Tetrahydro-1H-pyrrolo[1,2-c]imidazol-3(2H)-one

Costa Metallinos,* Seyed Iraj Sadraei, and Nadezda Zhukovskaya

*Department of Chemistry, Brock University, 500 Glenridge Ave., St. Catharines, Ontario, L2R 3K4, Canada

Abstract

An L-proline-derived imidazolone protected with an N-triethylsilyl (N-TES) group undergoes diastereoselective lithiationelectrophile quench to give C5-substituted products with syn stereochemistry. Unlike the previous N-t-Bu analogues, the N-TES derivatives may be easily N-desilylated to give secondary ureas that serve as precursors to N-phenyl chiral bicyclic guanidines.