81480-61-7Relevant academic research and scientific papers
Diastereoselective synthesis of 2,5-dimethylpyrrolidines and 2,6- dimethylpiperidines by reductive amination of 2,5-hexanedione and 2,6- heptanedione with hydride reagents
Boga,Manescalchi,Savoia
, p. 4709 - 4722 (1994)
The reductive amination of 2,5-hexanedione and 2,6-heptanedione with ammonia and primary amines in the presence of hydride reagents afforded 2,5- dimethylpyrrolidines and 2,6-dimethylpiperidines with variable diastereoselectivity, as the cis/trans ratio was affected by the size of the ring formed and the steric and electronic properties of the nitrogen substituent. Increasing the bulkiness of the nitrogen substituent, the cis pyrrolidines and the trans-piperidines were obtained with enhanced selectivity.
One-Pot Synthesis of Substituted Pyrrolidines via Aminomercuration-Demercuration of 1,4- and 1,5-Hexadiene
Barluenga, J.,Najera, C.,Yus, M.
, p. 1297 - 1299 (2007/10/02)
The aminomercuratione-demercuration of 1,4- and 1,5-hexadiene yield cis- and trans-2,5-dimethyl-N-arylpyrrolidines via one-pot process.The intermolecular cyclization reaction goes through the corresponding mercurated pyrrolidines; these intermediates were isolated and characterized when the mercuration reaction was completed.The high stereoselectivity observed allows an easy way of synthesis for N-substituted trans-2,5-dimethylpyrrolidines.
