885044-27-9Relevant academic research and scientific papers
Synthetic applications and inversion dynamics of configurationally stable 2-lithio-2-arylpyrrolidines and -piperidines
Beng, Timothy K.,Woo, Jin Sun,Gawley, Robert E.
, p. 14764 - 14771 (2012)
In diethyl ether, N-Boc-2-lithio-2-arylpiperidines have been found to be configurationally stable at -80 °C, whereas N-Boc-2-lithio-2- arylpyrrolidines are configurationally stable at -60 °C. Several tertiary benzylic carbanions derived from enantioenriched 2-aryl heterocycles have been successfully alkylated or acylated with little to no loss of enantiopurity. The scope of the reactions has been explored. The enantiomerization dynamics of N-Boc-2-lithio-2-phenylpyrrolidine and N-Boc-2-lithio-2-phenylpiperidine have been studied in the presence of different solvents and achiral ligands.
