A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions

Journal of the Brazilian Chemical Society

Jeronimo S. Costa¹  Bruno S. Freire²  André L. S. Moura²  Vera L. Patrocinio Pereira² 

[1] ,Universidade Federal do Rio de Janeiro Centro de Ciências da Saúde Núcleo de Pesquisas de Produtos NaturaisRio de Janeiro RJ ,Brazil

关键词: nitroalkyl anions;    Michael addition;    Nef reaction;    tetrabutylammonium fluoride;   

DOI  :  10.1590/S0103-50532006000700006

来源: SciELO

【 摘 要 】

The reactivity and diastereoselectivity of conjugate addition of different nitronates ions to (R)-carvone was systematically studied. The Michael adducts 2a-e were obtained in good yield and 3,2-cis-3,5-trans selectivity. The nitroadducts 2b,c were transformed via Nef reaction into (R)-carvone ketone derivatives 9,10 and nitroadducts 2b,d led to (R)-carvone alkylated derivatives 11,12, via a denitration reaction.

【 授权许可】

CC BY   
 All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License