Michael additions of thiocompounds to α, β-unsaturated carbonyl compounds in aqueous media: stereoselectivity with unambiguous characterization by NMR

Journal of the Brazilian Chemical Society

Instituto de Tecnologia em Fármacos, Rio de Janeiro, Brazil¹  Almeida, Queli Aparecida Rodrigues de¹  Coelho, Ricardo Bezerra¹  Kaiser, Carlos Roland¹  Jones Junior, Joel¹  Silva, Flavia Martins da¹  Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil¹  Carvalho, Erika Martins de¹  Pereira, Maria Luiza de Oliveira¹ 

关键词: 1;    4-additions;    water;    Green Chemistry;    NMR;   

DOI  :  10.1590/S0103-50532008000500013

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

The reactions of crotonaldehyde (8) with thiophenol (2) and benzalacetone (10) with ethane-1,2-dithiol (11) yield Michael addition products. The reactions of thiophenol (2) with (R)-carvone (13) and (S)-perillaldehyde (15) lead to (2S,3R,5S)-5-isopropenyl-2-methyl-3-(phenylthio)cyclohexanone (14) and (1R,2R,4S)-4-isopropenyl-2-(phenylthio)cyclohexanecarbaldehyde (16), respectively. An unambiguous elucidation of the stereochemistry of 14 and 16 by NMR is also presented.

【 授权许可】

Unknown