tert-Butyl (2R)-2-(1H-imidazole-1-carbonyl)pyrrolidine-1-carboxylate

CAS 2361127-34-4, Cat. No EN300-52233921

Reagent for C2-functionalization of pyridines

tert-Butyl (2R)-2-(1H-imidazole-1-carbonyl)pyrrolidine-1-carboxylate is a reagent used in the site-selective C2-functionalization of pyridines¹. It acts as an electrophilic partner in reactions with (pyridine-2-yl)phosphonium salts, enabling the installation of carbonyl-containing fragments under mild, metal-free conditions. The reagent supports an umpolung strategy that avoids organometallics usage, making the process more practical and functional group tolerant. It is useful for modifying pyridines and quinolines, leading to an enlargement of synthetic pharmaceutical and ligand design options.

Synonyms: tert-butyl (R)-2-(1H-imidazole-1-carbonyl)pyrrolidine-1-carboxylate; 1-pyrrolidinecarboxylic acid, 2-(1H-imidazol-1-ylcarbonyl)-, 1,1-dimethylethyl ester, (2R)-; 1,1-dimethylethyl (2R)-2-(1H-imidazol-1-ylcarbonyl)-1-pyrrolidinecarboxylate

Selected publication

1. From Pyridine-N-Oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy.Bugaenko, D. I.; Yurovskaya, M. A.; Karchava, A. V. Org Lett 2021, 23 (15), 6099–6104. DOI: 10.1021/acs.orglett.1c02165