Asymmetric Syntheses of 2-Substituted and 2,5-Disubstituted Pyrrolidines from (3S,5R,7aR)-5-(Benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine

Alan R. Katritzky; Xi-Lin Cui; Baozhen Yang; Peter J. Steel

doi:10.1021/jo9821426

Asymmetric Syntheses of 2-Substituted and 2,5-Disubstituted Pyrrolidines from (3S,5R,7aR)-5-(Benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine

J Org Chem. 1999 Mar 19;64(6):1979-1985. doi: 10.1021/jo9821426.

Authors

Alan R. Katritzky¹, Xi-Lin Cui, Baozhen Yang, Peter J. Steel

Affiliation

¹ Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, and Department of Chemistry, University of Canterbury, Christchurch, New Zealand.

PMID: 11674292
DOI: 10.1021/jo9821426

Abstract

Benzotriazole, 2,5-dimethoxytetrahydrofuran, and (S)-phenylglycinol in one step gave 80% of (3S, 5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl-[2,1-b]oxazolopyrrolidine (6), whose crystal structure was confirmed by X-ray crystallography. Novel chiral pyrrolidine synthon 6 reacts with organosilicon (allyltrimethylsilanes and vinyloxytrimethylsilanes), organophosphorus, organozinc, and Grignard reagents to afford chiral 2-substituted and 2,5-disubstituted pyrrolidines.