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The highly enantioselective 1,3-dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde catalyzed by hybrid diamines
Journal article   Peer reviewed

The highly enantioselective 1,3-dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde catalyzed by hybrid diamines

Łukasz Weseliński, Edyta Słyk, Janusz Jurczak and Lukasz Jan Weselinski
Tetrahedron letters, Vol.52(3), pp.381-384
19/01/2011
DOI: https://doi.org/10.1016/j.tetlet.2010.11.015

Abstract

1,3-Dipolar cycloaddition Amino acids Asymmetric organocatalysis Binaphthyl derivatives Nitrones
1,3-Dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde can be catalyzed by hybrid diamines, obtained from (S)-BINAM and l-α-amino acids. The hybrid of (S)-BINAM and l-Phe was found to be the best organocatalyst. Products were obtained in good yield and diastereoselectivity as well as high enantioselectivity (82–91% ee). Subsequent transformations into functionalized pyrrolidinones have been demonstrated.

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