Chiral Brønsted Acid Catalyzed Highly Stereoselective Mannich-type reaction of Azlactone with Aldimines

Chiral Brønsted Acid Catalyzed Highly Stereoselective Mannich-type reaction of Azlactone with Aldimines

Gonçalves, Vanessa P.; Justo, Rodrigo M. S.; Amarante, Giovanni W.

Abstract:

The asymmetric Mannich reaction is one of the most powerful carbon-carbon bond reactions in organic synthesis. The resulting β-amino carbonyls products are key intermediates in the preparation of biologically chiral amines such as α,β-diamino acids. The organocatalytic version of this reaction presents a series of advantages, such as high yields and enantioselectivities, free-metal catalysts and environment-friendly conditions. In this work we report the Mannich-type reaction between azlactone and aldimines, employing a chiral phosphoric acid as organocatalyst.

The asymmetric Mannich reaction is one of the most powerful carbon-carbon bond reactions in organic synthesis. The resulting β-amino carbonyls products are key intermediates in the preparation of biologically chiral amines such as α,β-diamino acids. The organocatalytic version of this reaction presents a series of advantages, such as high yields and enantioselectivities, free-metal catalysts and environment-friendly conditions. In this work we report the Mannich-type reaction between azlactone and aldimines, employing a chiral phosphoric acid as organocatalyst.

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DOI: 10.5151/chempro-15bmos-BMOS2013_20139216537

Referências bibliográficas

• [1] 1 Uraguchi, D.; Ueki, Y.; Ooi, T. J. Am. Chem. Soc. 2008, 130, 14088.
• [2] 2 Teo, Y.-C.; Lau, J.-J.; Wu, M.-C. Tetrahedron: Asymmetry 2008, 19, 186.
• [3] 3 Ávila, E. P.; De Mello, A. C.; Diniz, R.; Amarante, G. W. Eur. J. Org. Chem. 2013, 10, 1881.

Como citar:

Gonçalves, Vanessa P.; Justo, Rodrigo M. S.; Amarante, Giovanni W.; "Chiral Brønsted Acid Catalyzed Highly Stereoselective Mannich-type reaction of Azlactone with Aldimines", p-16-16. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_20139216537