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

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

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.

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Bibliographic Details
Main Authors: Almeida,Queli Aparecida Rodrigues de, Pereira,Maria Luiza de Oliveira, Coelho,Ricardo Bezerra, Carvalho,Erika Martins de, Kaiser,Carlos Roland, Jones Junior,Joel, Silva,Flavia Martins da
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2008
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000500013
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