Studies on the reduction of beta-enamino ketones

Journal of the Brazilian Chemical Society

Melina A. Machado¹  Maria Inês N. C. Harris¹  Antonio C. H. Braga¹ 

[1] ,Universidade Estadual de Campinas Instituto de Química Campinas SP ,Brazil

关键词: amino alcohols;    enamino ketones;    amino ketones;    Mannich base;   

DOI  :  10.1590/S0103-50532006000700036

来源: SciELO

【 摘 要 】

Reduction of beta-enamino ketones 1 with NaBH(OAc)3 in glacial acetic acid gave beta-amino ketones 3 in 65% to 67% yield. These data and others observed in the reduction of beta-enamino ketones 1 to preferentially syn gamma-amino alcohols 2 with NaBH4/HOAc suggest that in this last reaction we have firstly the reduction of the beta-enamino ketones 1 to produce the beta-amino ketones 3, and then this compound is reduced to the gamma-amino alcohols 2. We can say from this results that the diastereosselectivity of the reduction of beta-enamino ketones 1 to mainly syn gamma-amino álcohols 2, can be analysed as a competition between a chair-like transition state and a boat-like transition state, obtained from the beta-amino ketones 3.

【 授权许可】

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