Ugi Reaction of Natural Amino Acids Promoted by NbCl5

Ugi Reaction of Natural Amino Acids Promoted by NbCl5

Sena, Milenna M.; Andrade, Carlos Kleber Z.; Rocha, Rafael O.

Abstract:

Multicomponent Reactions (MCR) are useful reactions to obtain complex products by a simple mixture of 3 or more reactants. Classic Ugi reaction (4-UCR) involves a mixture of an amine, aldehyde, isocyanide and a carboxylic acid giving peptoides as products. Some modifications on the components such as the use of amino acids and Lewis acids like titanium (IV) chloride have been reported to induced stereoselectivity in good ratio. Niobium (V) pentachloride have been reported as an efficient Lewis acid to promote several organic reactions. This led us to investigate the use of NbCl5 as Lewis acid and its ability to induce the new chiral center formed in the Ugi reaction using natural amino acids, aldehyde, isocyanide and methanol as a forth component.

Multicomponent Reactions (MCR) are useful reactions to obtain complex products by a simple mixture of 3 or more reactants. Classic Ugi reaction (4-UCR) involves a mixture of an amine, aldehyde, isocyanide and a carboxylic acid giving peptoides as products. Some modifications on the components such as the use of amino acids and Lewis acids like titanium (IV) chloride have been reported to induced stereoselectivity in good ratio. Niobium (V) pentachloride have been reported as an efficient Lewis acid to promote several organic reactions. This led us to investigate the use of NbCl5 as Lewis acid and its ability to induce the new chiral center formed in the Ugi reaction using natural amino acids, aldehyde, isocyanide and methanol as a forth component.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0367-1

Referências bibliográficas

• [1] 1 Domling, A. Chem. Rev. 2006, 106, 17.
• [2] 2 Godet, T.; Bonivn, Y.; Vincent, G.; Merle, D.; Thozet, A.; Ciufolini, M. A. Org. Lett. 2004, 6, 3281.
• [3] 3 a) Andrade, C. K. Z.; Rocha, R. O. Mini Rev. Org. Chem. 2006, 3, 271. b) Andrade, C. K. Z. Curr. Org. Synth. 2004, 1, 333.

Como citar:

Sena, Milenna M.; Andrade, Carlos Kleber Z.; Rocha, Rafael O.; "Ugi Reaction of Natural Amino Acids Promoted by NbCl5", p-367-367. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0367-1