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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Sociedade Brasileira de Química
2008
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oai:scielo:S0103-505320080005000132008-08-05Michael additions of thiocompounds to α, β-unsaturated carbonyl compounds in aqueous media: stereoselectivity with unambiguous characterization by NMRAlmeida,Queli Aparecida Rodrigues dePereira,Maria Luiza de OliveiraCoelho,Ricardo BezerraCarvalho,Erika Martins deKaiser,Carlos RolandJones Junior,JoelSilva,Flavia Martins da 1,4-additions water Green Chemistry 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.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.19 n.5 20082008-01-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000500013en10.1590/S0103-50532008000500013 |
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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 |
| spellingShingle |
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 Michael additions of thiocompounds to α, β-unsaturated carbonyl compounds in aqueous media: stereoselectivity with unambiguous characterization by NMR |
| author_facet |
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 |
| author_sort |
Almeida,Queli Aparecida Rodrigues de |
| title |
Michael additions of thiocompounds to α, β-unsaturated carbonyl compounds in aqueous media: stereoselectivity with unambiguous characterization by NMR |
| title_short |
Michael additions of thiocompounds to α, β-unsaturated carbonyl compounds in aqueous media: stereoselectivity with unambiguous characterization by NMR |
| title_full |
Michael additions of thiocompounds to α, β-unsaturated carbonyl compounds in aqueous media: stereoselectivity with unambiguous characterization by NMR |
| title_fullStr |
Michael additions of thiocompounds to α, β-unsaturated carbonyl compounds in aqueous media: stereoselectivity with unambiguous characterization by NMR |
| title_full_unstemmed |
Michael additions of thiocompounds to α, β-unsaturated carbonyl compounds in aqueous media: stereoselectivity with unambiguous characterization by NMR |
| title_sort |
michael additions of thiocompounds to α, β-unsaturated carbonyl compounds in aqueous media: stereoselectivity with unambiguous characterization by nmr |
| description |
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. |
| publisher |
Sociedade Brasileira de Química |
| publishDate |
2008 |
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http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000500013 |
| work_keys_str_mv |
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