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

Queli Aparecida Rodrigues De Almeida²  Maria Luiza De Oliveira Pereira²  Ricardo Bezerra Coelho²  Erika Martins De Carvalho¹  Carlos Roland Kaiser²  Joel Jones Junior²  Flavia Martins Da Silva² 

[1] ,Universidade Federal do Rio de Janeiro Instituto de Química Departamento de Química OrgânicaRio de Janeiro RJ ,Brazil

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

DOI  :  10.1590/S0103-50532008000500013

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】

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