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. ©2008 Sociedade Brasileira de Química.
CITATION STYLE
De Almeida, Q. A. R., Pereira, M. L. D. O., Coelho, R. B., De Carvalho, E. M., Kaiser, C. R., Jones, J., & Da Silva, F. M. (2008). 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, 19(5), 894–902. https://doi.org/10.1590/s0103-50532008000500013
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