Michael Additions of Aldehydes and Ketones to β-Nitrostyrenes in an Ionic Liquid

Michael additions of different aldehydes and ketones to β‐nitrostyrene and 2‐(β‐nitrovinyl)thiophene in 1‐butyl‐3‐methylimidazolium hexafluorophosphate ([bmim]PF6) were studied. β‐Nitrostyrene was a better acceptor than 2‐(β‐nitrovinyl)thiophene, in terms of both reactivity and selectivity. Aldehyde...

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Bibliographic Details
Published in:European journal of organic chemistry 2004-04, Vol.2004 (7), p.1577-1583
Main Authors: Kotrusz, Peter, Toma, Stefan, Schmalz, Hans-Günther, Adler, Andreas
Format: Article
Language:English
Subjects:
Ionic liquids
L-Proline
Michael additions
Organocatalysis
β-Nitrostyrenes
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Summary:Michael additions of different aldehydes and ketones to β‐nitrostyrene and 2‐(β‐nitrovinyl)thiophene in 1‐butyl‐3‐methylimidazolium hexafluorophosphate ([bmim]PF6) were studied. β‐Nitrostyrene was a better acceptor than 2‐(β‐nitrovinyl)thiophene, in terms of both reactivity and selectivity. Aldehydes proved to be better donors than ketones, which were themselves better than β‐diketones. L‐proline proved to be the best catalyst among seven organocatalysts tested. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300648