C. Boga, F. Manescalchi, D. Savoia
Apr 18, 1994
Citations
0
Influential Citations
20
Citations
Journal
Tetrahedron
Abstract
Abstract The reductive amination of 2,5-hexanedione and 2,6-heptanedione with ammonia and primary amines in the presence of hydride regents afforded 2,5-dimethylpyrrolidines and 2,6-dimethylpiperidines with variable diastercoselectivity, 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.