Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3

Journal of the Brazilian Chemical Society

Carlos Kleber Z. Andrade¹  Otilie E. Vercillo¹  Juliana P. Rodrigues¹  Denise P. Silveira¹ 

[1] ,Universidade de Brasília Instituto de Química Brasília DF ,Brazil

关键词: citronellal;    isopulegol;    intramolecular ene reactions;    Lewis acids;    selectivity;   

DOI  :  10.1590/S0103-50532004000600005

来源: SciELO

【 摘 要 】

Niobium pentachloride, tantalum pentachloride and indium trichloride efficiently catalysed the cyclization of (R)-citronellal to a mixture of isopulegol and neoisopulegol in good yields. A comparative study was carried out which demonstrated that NbCl5 is the most active Lewis acid whereas InCl3 is the most selective one. The selectivity of the reactions varied according to the Lewis acid used and to the solvent. The ene reaction of a 1,7-diene was also investigated. In this case, all Lewis acids tested showed excellent selectivity.

【 授权许可】

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