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Showing papers on "Wieland–Miescher ketone published in 2009"


Journal ArticleDOI
TL;DR: In this paper, the authors presented a study that was supported by the Ministerio de Ciencia e Innovació (Spain)-FEDER through projects CTQ2007-67661338/BQU, CTQ 2007-62771 /BQU and Consolider Ingenio 2010 CSD2007-00006.
Abstract: This research was supported by the Ministerio de Ciencia e Innovacion (Spain)-FEDER through projects CTQ2007- 61338/BQU, CTQ2007-62771/BQU and Consolider Ingenio 2010 CSD2007-00006. Thanks are also due to the Comissionat per a Universitats i Recerca (Catalonia) for Grant 2005SGR-00442, Generalitat Valenciana for Grant (GVPRE/ 2008/006) and the University of Alicante (GRJ06-05).

55 citations


Journal ArticleDOI
TL;DR: In this article, Imidazolidinones derived from the reaction of the catalyst and enamines have been found as intermediates in these reactions, and they have been shown to induce enantiomeric excesses in intramolecular aldol condensations.

38 citations


Journal ArticleDOI
TL;DR: In this paper, the enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and Bronsted acid to prepare Wieland-Miescher ketone was examined in detail.
Abstract: New or known N-benzyl-N-(2-pyrrolidinylmethyl)amine derivatives bearing a variety of substituents on the aromatic ring were easily prepared from N-Boc-proline or N-Boc-prolinol. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and Bronsted acid to prepare Wieland-Miescher ketone was examined in detail. During the examination, remarkable substitutional effects on the aromatic ring were observed. Development of a catalytic version of the reaction was successfully achieved by the use of N-[(9-anthracenyl)methyl]-N-(2-pyrrolidinyl-methyl)amine in the presence of dichloroacetic acid.

11 citations