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Diastereoselective synthesis of 2,5-dimethylpyrrolidines and 2,6-dimethylpiperidines by reductive amination of 2,5-hexanedione and 2,6-heptanedione with hydride reagents

✍ Scribed by Carla Boga; Francesco Manescalchi; Diego Savoia

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 1013 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)85010-9

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✦ Synopsis

The reductive amination of 25hexanedione and 2,6-heptanedione with ammonia and primary amines in the presence of hydride reagents afforded 2,!5dimethylpyrrolidines and 2.6-dimethylpipexidines with variable diastereoselectivity, as the cislrrans 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 rran.-piperidines were obtained with enhanced selectivity.

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