Multicomponent Synthesis of Bifunctional Thiourea Organocatalysts for the Enantioselective Aldol Reaction

Multicomponent Synthesis of Bifunctional Thiourea Organocatalysts for the Enantioselective Aldol Reaction

Silva, Tiago Lima da; Schneider, Paulo Henrique

Abstract:

During the past decade the field of organic chemistry has witnessed a tremendous rise in the number of synthetic applications of organocatalysis. In this scenario, L-proline has proved to be an important and versatile organocatalyst for applications in different types of reactions. The amino acid derivative, thiazolidine, has equivalent efficiency, versatility and cost when compared to the natural amino acid L-proline according to the literature. Thioureas, as bifunctional organocatalyst, brings a functional chelating hydrogen bond in the thiourea portion and an asymmetric induction is achieved by a highly ordered transition state. Organocatalysis using thioureas catalysts may replace earlier methods used for the asymmetric synthesis of aldol products, in which metal catalysts were used, resulting in a greener production of the same molecules. In this work we present our initial results on the synthesis of new bifunctional organocatalysts 6, based on thiazolidine, for the enantioselective aldol reaction.

During the past decade the field of organic chemistry has witnessed a tremendous rise in the number of synthetic applications of organocatalysis. In this scenario, L-proline has proved to be an important and versatile organocatalyst for applications in different types of reactions. The amino acid derivative, thiazolidine, has equivalent efficiency, versatility and cost when compared to the natural amino acid L-proline according to the literature. Thioureas, as bifunctional organocatalyst, brings a functional chelating hydrogen bond in the thiourea portion and an asymmetric induction is achieved by a highly ordered transition state. Organocatalysis using thioureas catalysts may replace earlier methods used for the asymmetric synthesis of aldol products, in which metal catalysts were used, resulting in a greener production of the same molecules. In this work we present our initial results on the synthesis of new bifunctional organocatalysts 6, based on thiazolidine, for the enantioselective aldol reaction.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0012-1

Referências bibliográficas

• [1] 1Taylor, M. S;Jacobsen. E. N.Angew. Chem. Int. Ed. 2006, 45, 1520 – 1543
• [2] 2 Rambo,R. S.; Schneider,P. H. Tetrah Asym.. 2010. v.21,p. 2254-2257.
• [3] 3 Stephen J. Connon. Chem. Eur. J. 2006, 12, 5418 –5427.

Como citar:

Silva, Tiago Lima da; Schneider, Paulo Henrique; "Multicomponent Synthesis of Bifunctional Thiourea Organocatalysts for the Enantioselective Aldol Reaction", p-12-12. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0012-1