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. © 1993.
Boga, C., Manescalchi, F., Savoia, D. (1994). Diastereoselective synthesis of 2,5-dimethylpyrrolidines and 2,6-dimethylpiperidines by reductive amination of 2,5-hexanedione and 2,6-heptanedione with hydride reagents. TETRAHEDRON, 50(16), 4709-4722 [10.1016/S0040-4020(01)85010-9].
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 C.;Manescalchi F.;Savoia D.
1994
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. © 1993.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
