Highly enantioselective arylation of aromatic aldehydes, promoted by chiral phosphinite ligands

Highly enantioselective arylation of aromatic aldehydes, promoted by chiral phosphinite ligands

Soares, Liliana A.; Salles, Helena D. de; Schneider, Paulo H.

Abstract:

Enantiopure compounds production is becoming increasingly important, and for this purpose the asymmetric synthesis, particularly asymmetric catalysis, have been highlighted as an efficient method. In this context the nucleophilic addition to carbonyl compounds have received much attention, specially the asymmetric arylation of aldehydes and ketones. In this work we present the synthesis of new phosphinite ligands with an oxazolidinic ring in its structure. In order to modulate the structure of the ligands aiming the optimization of the asymmetric induction, based on a six member ring N,P transition state, some variations of substituents in strategic positions of the basic structure of the ligand were made.

Enantiopure compounds production is becoming increasingly important, and for this purpose the asymmetric synthesis, particularly asymmetric catalysis, have been highlighted as an efficient method. In this context the nucleophilic addition to carbonyl compounds have received much attention, specially the asymmetric arylation of aldehydes and ketones. In this work we present the synthesis of new phosphinite ligands with an oxazolidinic ring in its structure. In order to modulate the structure of the ligands aiming the optimization of the asymmetric induction, based on a six member ring N,P transition state, some variations of substituents in strategic positions of the basic structure of the ligand were made.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0018-1

Referências bibliográficas

• [1] 1 Paixão, M. W. , Braga, A. L., Lüdtke, D. S. J. Braz. Chem. Soc., 2008, 5, 813.
• [2] 2 Bolm, C.; Gladysz, J., Eds. Chem. Rev. 2003, 103, 2761
• [3] 3 Rudolph, J.; Bolm, C.; Norrby, P. O. J. Am. Chem. Soc. 2005, 127, 1548.
• [4] 4 Fontes, M. Verdaguer, x. Solá , L. Pericás, M. A. Riera, A. J. Org.Chem. 2004, 69, 253

Como citar:

Soares, Liliana A.; Salles, Helena D. de; Schneider, Paulo H.; "Highly enantioselective arylation of aromatic aldehydes, promoted by chiral phosphinite ligands", p-18-18. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0018-1