Diastereoselective synthesis of 2,5-dimethylpyrrolidines and 2,6-dimethylpiperidines by reductive amination of 2,5-hexanedione and 2,6-HEPTANEDIONE (cas 13505-34-5) with hydride reagents

Add time:08/08/2019    Source:sciencedirect.com

The reductive amination of 2,5-hexanedione and 2,6-HEPTANEDIONE (cas 13505-34-5) 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.

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