Tetrahedron p. 4709 - 4722 (1994)
Update date:2022-08-04
Topics: Diastereoselective Reductive Amination 2,5-dimethylpyrrolidines 2,6-dimethylpiperidines 2,5-hexanedione 2,6-heptanedione Hydride reagents
Boga
Manescalchi
Savoia
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.
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